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

HRID 650470ノート

反応式

HRID 650470 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-417b1d7bb7c04281b6b8e435316c9186
出典データセット
uspto-grants-2001_08
特許番号
US06274336B1

反応ノート

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