1,2-Dichloroethane → 3-hydroxy-4-[N-[(phenylmethoxy)carbonyl]-L-leucyl]-1-pyrrolidinecarboxylic acid 1,1dimethylethyl ester

HRID 650470노트

반응식

HRID 650470 반응식
[OH:1][CH:2]1[CH:6](N)[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[C:15]([NH:25][C@H:26]([C:31](O)=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CCOC(C)=O>[CH3:12][C:11]([O:10][C:8]([N:4]1[CH2:5][CH:6]([C:31](=[O:32])[C@H:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[NH:25][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH:2]([OH:1])[CH2:3]1)=[O:9])([CH3:14])[CH3:13]

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 757711-HydroxybenzotriazoleHCID 11229445tert-Butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 541360223-hydroxy-4-[N-[(phenylmethoxy)carbonyl]-L-leucyl]-1-pyrrolidinecarboxylic acid 1,1dimethylethyl ester수율 65.6%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-hydroxy-4-amino-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester (202 mg, 1.14 mmol) in CH2CI2 (5 mL) was added CBZ-leucine (302.9 mg, 1.14 mmol), HOBT (154 mg, 1.14 mmol) and EDC (262.2 mg, 1.37 mmol). The reaction was allowed to stir until complete by TLC analysis whereupon it was diluted with EtOAc and washed sequentially with pH 4 buffer, sat. K2CO3, water and brine. The organic layer was dried (MgSO4), filtered and concentrated. Column chromatography of the residue (3:1 EtOAc:hexanes) gave 325 mg of the title compound: MS (ES+) 450.3 (MH+), 472.2 (M+Na).

후처리

  1. washwashed sequentially with pH 4 buffer
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-417b1d7bb7c04281b6b8e435316c9186
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06274336B1

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