Water → (2'S,3'R,4'S,5'R)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid [4-(2-methanesulfonyl-ethoxy)-2-methoxy-phenyl]-amide

HRID 417329노트

반응식

HRID 417329 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][S:12][CH3:13])[CH:6]=[CH:5][C:4]=1[NH:14][C:15]([C@@H:17]1[NH:21][C@@H:20]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C@:19]2([C:34]3[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=3)[NH:28][C:27]2=[O:36])[C@H:18]1[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[C:38]=1[F:44])=[O:16].ClC1C=C(C=CC=1)C(OO)=[O:50].[OH2:56]>ClCCl>[CH3:13][S:12]([CH2:11][CH2:10][O:9][C:7]1[CH:6]=[CH:5][C:4]([NH:14][C:15]([C@@H:17]2[NH:21][C@@H:20]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C@:19]3([C:34]4[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=4)[NH:28][C:27]3=[O:36])[C@H:18]2[C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[C:38]=2[F:44])=[O:16])=[C:3]([O:2][CH3:1])[CH:8]=1)(=[O:50])=[O:56]

참가 물질

5

반응물 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 58286316(2'S,3'R,4'S,5'R)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid [2-methoxy-4-(2-methylsulfanyl-ethoxy)-phenyl]-amide

생성물 1

HCID 58286304(2'S,3'R,4'S,5'R)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid [4-(2-methanesulfonyl-ethoxy)-2-methoxy-phenyl]-amide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of chiral (2′S,3′R,4′S,5′R)-6-chloro-4′-(3-chloro-2-fluoro-phenyl)-2′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid [2-methoxy-4-(2-methylsulfanyl-ethoxy)-phenyl]-amide (0.17 g, 0.26 mmol) prepared in Example 169 in dichloromethane (5 mL) was added 3-chloroperoxybenzoic acid (MCPBA, Aldrich, 77%) (0.11 g mL, 0.52 mmol). The reaction mixture was stirred at room temperature for 2 h. The crude mixture was diluted with water, and extracted with dichloremethane three times. The combined organic extract was washed with aqueous saturated Na2S2O3 solution, brine, dried over MgSO4, and concentrated. TLC analysis indicated the complete consumption of starting material and the formation of two major products. The residue was purified by chromatography (0-50% EtOAc in dichlormethane) to give the first product chiral (2′S,3′R,4′S,5′R)-6-chloro-4′-(3-chloro-2-fluoro-phenyl)-2′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid [4-(2-methanesulfonyl-ethoxy)-2-methoxy-phenyl]-amide as a light red solid (Yield, 98 mg, 55%).

후처리

  1. extractionextracted with dichloremethane three times
  2. extractionThe combined organic extract
  3. washwas washed with aqueous saturated Na2S2O3 solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customthe complete consumption of starting material
  7. customThe residue was purified by chromatography (0-50% EtOAc in dichlormethane)
  8. customto give

출처 및 근거

ORD 기록
ord-c71d6b63bed043b1854701b9ba12a200
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088815B2

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