Trifluoroacetic acid → rac-(2'S,3'R,4'S,5'R)-2'-(3-acetoxy-2,2-dimethyl-propyl)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid trifluoroacetic acid

HRID 417258ノート

反応式

HRID 417258 の反応式
C([O:5][C:6]([CH:8]1[NH:12][CH:11]([CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15][O:16][C:17](=[O:19])[CH3:18])[C:10]2([C:29]3[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=3)[NH:23][C:22]2=[O:31])[CH:9]1[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=1[F:39])=[O:7])(C)(C)C.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>ClCCl>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[C:17]([O:16][CH2:15][C:14]([CH3:21])([CH3:20])[CH2:13][CH:11]1[C:10]2([C:29]3[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=3)[NH:23][C:22]2=[O:31])[CH:9]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=2[F:39])[CH:8]([C:6]([OH:7])=[O:5])[NH:12]1)(=[O:19])[CH3:18]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 66625386rac-(2'S,3'R,4'S,5'R)-2'-(3-acetoxy-2,2-dimethyl-propyl)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid tert-butyl ester

生成物 1

HCID 86653943rac-(2'S,3'R,4'S,5'R)-2'-(3-acetoxy-2,2-dimethyl-propyl)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid trifluoroacetic acid収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of rac-(2′S,3′R,4′S,5′R)-2′-(3-acetoxy-2,2-dimethyl-propyl)-6-chloro-4′-(3-chloro-2-fluoro-phenyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid tert-butyl ester (0.24 g, 0.41 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (1 g). The reaction mixture was stirred at room temperature for 18 h, then concentrated. The residue was then triturated with ethyl ether hexanes, concentrated, dried in vacuo to give rac-(2′S,3′R,4′S,5′R)-2′-(3-acetoxy-2,2-dimethyl-propyl)-6-chloro-4′-(3-chloro-2-fluoro-phenyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid trifluoroacetic acid as a yellow solid (0.25 g, 97%).

後処理

  1. concentrationconcentrated
  2. customThe residue was then triturated with ethyl ether hexanes
  3. concentrationconcentrated
  4. customdried in vacuo

出典と根拠

ORDレコード
ord-733f63c066db4c7cb6f5c773f9890c55
出典データセット
uspto-grants-2012_01
特許番号
US08088815B2

反応ノート

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