Benzyl chloroformate → (2S,4S)-1-tert-Butyl 2-methyl 4-(((benzyloxy)carbonyl)amino)pyrrolidine-1,2-dicarboxylate

HRID 425128노트

반응식

HRID 425128 반응식
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH2:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].CCN(C(C)C)C(C)C.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10][C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 5200425(2S,4S)-1-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

생성물 1

HCID 57648857(2S,4S)-1-tert-Butyl 2-methyl 4-(((benzyloxy)carbonyl)amino)pyrrolidine-1,2-dicarboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(2S,4S)-4-Aminopyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-methyl ester (7.3 g, 30 mmol) was dissolved in DCM (100 mL) and cooled in an ice bath. DIPEA (3 equiv) was added, followed by benzyl chloroformate (1 equiv). The mixture was stirred at room temperature for 3 hours and then diluted with DCM (200 mL). The solution was washed with 1M HCl (100 mL), saturated aqueous NaHCO3 (100 mL) and saturated aqueous NaCl (100 mL), then dried over Na2SO4. The solvent was evaporated to afford the title compound (10.4 g, 28 mmol), which was used without further purification. MS m/z: [M+H]+ calcd for C12H21NO7S, 323.4. found 324.3.

후처리

  1. temperaturecooled in an ice bath
  2. washThe solution was washed with 1M HCl (100 mL), saturated aqueous NaHCO3 (100 mL) and saturated aqueous NaCl (100 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-f8f67199e6614adda0d0527f7f94a55f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106082B2

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