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[ CAS No. 209252-17-5 ] {[proInfo.proName]}

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Chemical Structure| 209252-17-5
Chemical Structure| 209252-17-5
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Product Details of [ 209252-17-5 ]

CAS No. :209252-17-5 MDL No. :MFCD01862860
Formula : C24H27NO6 Boiling Point : No data available
Linear Structure Formula :- InChI Key :-
M.W : 425.47 Pubchem ID :-
Synonyms :

Safety of [ 209252-17-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
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Application In Synthesis of [ 209252-17-5 ]

* 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.

  • Upstream synthesis route of [ 209252-17-5 ]
  • Downstream synthetic route of [ 209252-17-5 ]

[ 209252-17-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 244031-63-8 ]
  • [ 209252-17-5 ]
YieldReaction ConditionsOperation in experiment
1.3 g With silver benzoate In 1,4-dioxane; water for 0.5 h; Microwave irradiation Synthesis of (9H-fluoren-9-yl)methyl (R)-1-(carbonyl)-3-(tert-butoxycarbonyl)propan-2-ylcarbamate [4] [0138] aspartic acid(tBu)OH (2.0 g; 4.9 mmol; 1 eq.) was dissolved in anhydrous THF (20 ml). Net3 (0.74 ml; 5.4 mmol; 1.1 eq.) and ethylchloroformate (0.52 ml; 5.4 mmol; 1.1 eq.) were added sequentially at ?15° C. Stirring was continued for 15 min and then the solution was allowed to warm up to 0° C. In the mean time N-methylnitrosourea (2.5 g; 24.3 mmol; 5 eq.) is stirred in ice-cold Et2O (20 ml) and 40percent KOH (20 ml; ice-cold) is added dropwise until complete dissolution. The yellow diazomethane solution in Et2O was added dropwise at 0° C. to the amino acid solution and it was then allowed to warm up to RT and stirred for another 2.5 hours. Excess diazomethane was decomposed by dropwise addition of HOAc. The solution was washed with sat. NaHCO3, sat. NH4Cl, and brine. The organic layer was dried (Na2SO4) and evaporated under reduced pressure. The resulting diazo ketone was dissolved in water/dioxane (1:5; v/v; 160 ml). After addition of silver benzoate (0.12 g; 0.5 mmol; 0.1 eq.) the mixture was sonicated in an ultrasound bath until complete conversion (30 min) monitored by TLC (MeOH/DCM; 1:20; Rf: 0.1-0.2). After evaporation of dioxane under reduced pressure the solution was acidified with 5percent HCl and the precipitate extracted with EtOAc (three times). The organic layer was dried (Na2SO4) and evaporated under reduced pressure and the crude product purified by flash chromatography (MeOH/DCM; 1:20; Rf: 0.1-0.2) to yield [4] (1.3 g; 3.1 mmol; 63percent yield). [0140] 1H NMR (250 MHz, DMSO-d6): δ 12.2 (s, br, 1H,), 7.90 (d, 2H), 7.69 (dd, 2H), 7.42 (t, 2H), 7.33 (m, 3H), 4.27 (m, 3H), 3.59 (m, 1H), 2.41 (m, 4H), 1.38 (s, 9H), 13C NMR (75 MHz, DMSO-d6): 172.49, 170.24, 144.35, 141.19, 128.07, 127.51, 125.63, 120.56, 80.39, 65.80, 60.20, 47.17, 45.81, 28.13. Rt (10-100percent): 23.5 min. ESI (m+Na): 448.1.
Reference： [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 418 - 423
[2] Journal of the Chemical Society. Perkin Transactions 1, 2002, # 18, p. 2087 - 2089
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 7, p. 1691 - 1695
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 10, p. 2152 - 2158
[5] Synthesis, 1998, # 6, p. 837 - 841
[6] Tetrahedron Letters, 2003, vol. 44, # 32, p. 6079 - 6082
[7] Synthetic Communications, 2003, vol. 33, # 18, p. 3089 - 3096
[8] Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7648 - 7662
[9] Patent: US2014/39153, 2014, A1, . Location in patent: Paragraph 0138; 0139; 0140
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  • [ 71989-14-5 ]
  • [ 209252-17-5 ]
Reference： [1] Synthesis, 1998, # 6, p. 837 - 841
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7648 - 7662
[3] Patent: US2014/39153, 2014, A1,
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