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 417258노트

반응식

HRID 417258 반응식
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]

참가 물질

4

반응물 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

생성물 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 acid수율 97%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-733f63c066db4c7cb6f5c773f9890c55
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088815B2

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