ChemicalBook CAS DataBase List 1,2,4-Piperazinetricarboxylic acid,4-(1,1-dimethylethyl)2-methyl1-(phenylmethyl)ester,(2S)-

1,2,4-Piperazinetricarboxylic acid,4-(1,1-dimethylethyl)2-methyl1-(phenylmethyl)ester,(2S)- synthesis

5synthesis methods

Product Name:1,2,4-Piperazinetricarboxylic acid,4-(1,1-dimethylethyl)2-methyl1-(phenylmethyl)ester,(2S)-
CAS Number:314741-38-3
Molecular formula:C19H26N2O6
Molecular Weight:378.42

501-53-1
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$10.00/1g

848482-93-9 Synthesis

(S)-4-N-BOC-PIPERAZINE-2-CARBOXYLIC ACID

848482-93-9
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$9.00/100mg

74-88-4
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$15.00/10g

1,2,4-Piperazinetricarboxylic acid,4-(1,1-dimethylethyl)2-methyl1-(phenylmethyl)ester,(2S)-

314741-38-3
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$2359.00/5g

Yield:314741-38-3 100%

Reaction Conditions:

Stage #1: (S)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acidwith sodium hydrogencarbonate in water at 20; for 0.5 h;
Stage #2: benzyl chloroformate in 1,4-dioxane;water at 20;
Stage #3: methyl iodidewith potassium carbonate in N,N-dimethyl-formamide at 20; for 2 h;

Steps:

Intermediate 226-i: I -benzyl 4-(tert-butyl) 2-methyl (S)-pi perazine-I ,2,4- tricarboxylate

To a stirred suspension of (S)-4-/V-Boc-piperazine-2-carboxylic acid (502 mg, 2.18 mmol) in water (2.5 mL) was added NaHC0₃(366.2 mg, 4.36 mmol), and the resulting suspension was stirred at ambient temperature for 30 minutes. A solution of benzyl chloroformate (744 mg, 4.36 mmol) in dioxane (4 mL) was then added and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then diluted with water (5 mL) and extracted with EtOAc (2 15 mL). The combined organic layer was washed brine, dried over anhydrous Na₂S0₄, filtered and concentrated under reduced pressure. The remaining residue was then dissolved in DMF (7 mL) and K2CO3 (904 mg, 6.54 mmol) was added. After stirring for 5 minutes, CH3I (928 mg, 6.54 mmol) was added slowly and the resulting mixture was stirred at ambient temperature for 2 h. The reaction was quenched with H2O and extracted with EtOAc (2X 15 mL).The combined organic layer was washed with brine, dried over anhydrous Na₂S0₄, filtered and concentrated under reduced pressure to leave brown oil as the product (800 mg, quant.).¹H NMR (400 MHz, CDCI₃) δ 7.42 - 7.31 (m, 5H), 5.22 - 5.09 (m, 2H), 4.84 - 4.63 (m, 1 H), 4.63 - 4.47 (m, 1 H), 4.11 - 3.81 (m, 2H), 3.72 (d, J = 22.6 Hz, 3H), 3.32 (s, H), 3.08 (d, J = 13.5 Hz, H), .44 (s, 9H). Mass calculated for (Ci₉H26N₂0₆+H)⁺379.2, found 379.1.