Methanesulfonyl chloride → (2S,3S)-2-(3-Chloro-2-fluoro-benzylcarbamoyl)-3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1527337ノート

反応式

HRID 1527337 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[C@H:9]1[C:14](=[O:25])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[F:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][S:27](Cl)(=[O:29])=[O:28]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:27]([CH3:26])(=[O:29])=[O:28])[C@H:9]1[C:14](=[O:25])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[F:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 68283845(2S,3S)-2-(3-Chloro-2-fluoro-benzylcarbamoyl)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 86673824(2S,3S)-2-(3-Chloro-2-fluoro-benzylcarbamoyl)-3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

To an ice-cooled solution of (2S,3S)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.98 g, 2.64 mmol) in dry pyridine (13 mL) was added methanesulfonyl chloride (0.31 mL, 3.96 mmol). The reaction was stirred at 0° C. for 2 h and then at RT for 72 h. The volatiles were evaporated in vacuo and the residue was partitioned between water and EtOAc. The aqueous layer was repeatedly extracted with EtOAc, the combined organics were washed with 0.1N HCl and brine, dried (phase separator) and concentrated in vacuo to afford the title compound. Brown oil. MS (LC-MS): 451 [M+H]+, 395 [MH−tBu]+, 351 [MH−Boc]+; tR (HPLC conditions c): 5.08 min. The material thus obtained was used without any purification.

後処理

  1. waitat RT for 72 h
  2. customThe volatiles were evaporated in vacuo
  3. customthe residue was partitioned between water and EtOAc
  4. extractionThe aqueous layer was repeatedly extracted with EtOAc
  5. washthe combined organics were washed with 0.1N HCl and brine
  6. customdried (phase separator)
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-9c359254899f4e55969c25d87e6739c4
出典データセット
uspto-grants-2015_07
特許番号
US09085555B2

反応ノート

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