Bromopinacolone → (S)-2-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester 1-methyl ester

HRID 1908646ノート

反応式

HRID 1908646 の反応式
[CH3:1][O:2][C:3](=[O:29])[C@@H:4]([NH:14][C:15]([C:17]1[CH:21]=[C:20]([OH:22])[N:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].CC(C)([O-])C.[K+].Br[CH2:37][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:29])[C@@H:4]([NH:14][C:15]([C:17]1[CH:21]=[C:20]([O:22][CH2:37][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])[N:19]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:18]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

参加物

5

反応物 3

HCID 21642BromopinacoloneHCID 23665647Potassium tert-butoxideHCID 178501468HCID 178501468、化合物

生成物 1

HCID 66920060(S)-2-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester 1-methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Crude (S)-2-[(5-Hydroxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester (44 g) was dissolved in DMF and treated with 12.2 g potassium tert-butoxide and 14.7 ml 1-bromopinacolone. After 2 h the solvent was removed in vacuo, the residue taken up in DCM and extracted with water. The crude product obtained after evaporation of the solvent was purified by flash column chromatography on silica eluting with heptane/ethyl acetate giving the title compound as colorless oil (45 g).

後処理

  1. customAfter 2 h the solvent was removed in vacuo
  2. extractionextracted with water

出典と根拠

ORDレコード
ord-a13c9b70cec04809a99fb89fc9ce525c
出典データセット
uspto-grants-2013_12
特許番号
US08598179B2

反応ノート

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