(2-Oxopropyl)amine → (2S,4R)-4-tert-butoxy-2-(2-oxo-propylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1527914ノート

反応式

HRID 1527914 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:13][C@H:12]1[C:21](O)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][CH2:25][C:26](=[O:28])[CH3:27].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>ClCCl.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:13][C@H:12]1[C:21](=[O:22])[NH:24][CH2:25][C:26](=[O:28])[CH3:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 5

HCID 215(2-Oxopropyl)amineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6950951Z-Hyp(Tbu)-OH

生成物 1

HCID 89768391(2S,4R)-4-tert-butoxy-2-(2-oxo-propylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester収率 55.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of (2S,4R)-4-tert-butoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (10.78 g, 33.54 mmol) and 1-amino-propan-2-one (2.45 g, crude, 33.54 mmol) in dichlormethane (56 mL) were added EDC.HCl (6.405 g, 33.54 mmol), HOBt (5.128 g, 33.54 mmol) and triethylamine (12.67 mL, 100.62 mmol). The mixture was stirred at room temp. for 24 h. The reaction mixture was then diluted with water, extracted with dichloromethane and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude was then purified by column chromatography to give (2S,4R)-4-tert-butoxy-2-(2-oxo-propylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester (7 g, 55.4% yield) as a light brown liquid. MS calcd. for C20H29N2O5 [(M+H)+] 377.0, obsd. 377.4.

後処理

  1. extractionextracted with dichloromethane
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was then purified by column chromatography

出典と根拠

ORDレコード
ord-e03ec3c2181740448368411d3a020f83
出典データセット
uspto-grants-2015_07
特許番号
US09090559B2

反応ノート

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