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[ CAS No. 863971-53-3 ] {[proInfo.proName]}

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Chemical Structure| 863971-53-3
Chemical Structure| 863971-53-3
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Product Details of [ 863971-53-3 ]

CAS No. :863971-53-3 MDL No. :MFCD22200278
Formula : C40H42N6O10 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 766.80 Pubchem ID :-
Synonyms :

Safety of [ 863971-53-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 863971-53-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 863971-53-3 ]

[ 863971-53-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 474645-27-7 ]
  • [ 863971-53-3 ]
  • Fmoc-VC-PAB-MMAE [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 24h; A 100 ml RB flask was charged with <strong>[474645-27-7]monomethyl auristatin E</strong>(MMAE) (200 mg, 0.279 mmcl), 1-hydroxybenzotriazole (23.34 mg, 0.173 mmol) and Fmoc-Val-Cit-PAB-pnp (269 mg, 0.351 mmol). N,NDimethylformamide (8 ml) was added then the mixture was stirred at rt upon which N,N-diisopropylethylamine (0.12 1 ml, 0.696 mmol) was slowly added via a syringe. After 1 day at rt, LCMS showed almost completion. The solvent was evaporated under high vacuum. The crude was dissolved in DMF, loaded on celite and dried. It was purified by Isco (12 g column, eluent: EtOAc/Hexanes:0-100% then 100% then DCM/MeOH: 0-20% then 20%) to give the title compound 4-7 as an off-white solid (256 mg, 68% yield). LCMS [M+H] 1346.
68% With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; A 100 ml RB flask was charged with <strong>[474645-27-7]monomethyl auristatin E</strong> (MMAE) (200 mg,0.279 mmol),1-hydroxybenzotriazole(23.34 mg,0.173 mmol) and Fmoc-Val-Cit-PAB-pnp (269 mg,0.351 mmol). N,N-Dimethylformamide (8 ml) was added then the mixture was stirred at rt upon which A/,//-diisopropylethylamine (0.121 ml,0.696 mmol) was slowly added via a syringe. After 1 day at rt,LCMS showed almost completion. The solvent was evaporated under high vacuum. The crude was dissolved in a small volume of DMF,loaded on celite and dried. It was purified by Isco (12 g silica column,eluent: EtOAc/Hexanes: 0-100% then 100% followed by DCM/MeOH: 0-20% then 20%) to give the title compound as an off-white solid (256 mg,68% yield). LCMS [M+H]+ 1346.
With pyridine; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 24h;Inert atmosphere; To a solution of MMAE (0.15 g, 0.18 mmol) and Fmoc-Val-Cit-PAB-PNP 13 (0.152g, 0.19 mmol) in DMF (1.5 ml), was added HOBt (58 mg, 0.36 mmol), pyridine (0.12ml) and DIPEA (31 p1). The reaction mixture was stirred under N2 atmosphere at room temperature for 24h. Solvents were evaporated in vacuo and the residue triturated with ethyl acetate. The resulting solid was filtered, washed with ethyl acetate, dried to give 79. LC-MS ESI m/z 1367.7 [M+Na] This was used directlywithout further purification.
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 - 30℃; for 16h; To a 25 mL-round-bottom flask was added Fmocvc-PAB-PNP (2a) (0.33 g, 0.43 mmol) and anhydrous DMF (5 mL). To the solution were added MMAE (la, 0.21 g, 0.21 mmol), HOBt (38 mg, 0.28 mmol) and DIPEA (74 mg, 0.57 mmol) were added at 25 C. successively. The mixture was stirred at 25-30 C. for 16 hours until MMAE was totally consumed according to LCMS. The reaction mixture was filtered through membrane and the filtrate was purified by prep-HPLC (method A) to give Fmoc-3a as a white solid, which was dissolved in DMF (5 mL). To the solution was added diethylamine (0.3 mL). The reaction mixture was stirred at 30 C. for an hour until Fmoc was removed according to LCMS. The reaction mixture was filtered through membrane and the filtrate was purified by prepHPLC (method A) to give vcPAB-MMAE (3a) (0.20 g, 58% yield) as a white solid. ESI mlz: 562.5 (M/2+H).

  • 2
  • [ 474645-27-7 ]
  • [ 863971-53-3 ]
  • {4-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-5-(carbamoylamino)pentanamido]phenyl}methyl N-[(1S)-1-[(1S)-1-[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-2-[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]carbamoyl}-1-methoxy-2-methylethyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl](methyl)carbamoyl}-2-methylpropyl]carbamoyl}-2-methylpropyl]-N-methylcarbamate [ No CAS ]
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