Sodium Hydroxide → racemic (2'S,3S,4'R)-6-chloro-2'-(3-chlorophenyl)-4'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728078노트

반응식

HRID 1728078 반응식
C(OC([N:6]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([Cl:36])[CH:34]=2)[C:8]2([CH:13]([C:14]3[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=3[CH3:21])[CH2:12][C:11](=[O:22])[NH:10][CH:9]2[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[C:7]1=[O:37])=O)C.[OH-].[Na+]>CO>[Cl:36][C:33]1[CH:34]=[C:35]2[NH:6][C:7](=[O:37])[C:8]3([CH:13]([C:14]4[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=4[CH3:21])[CH2:12][C:11](=[O:22])[NH:10][CH:9]3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[C:30]2=[CH:31][CH:32]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 76567933racemic (2'S,3S,4'R)-6-chloro-2'-(3-chlorophenyl)-4'-(5-fluoro-2-methyl-phenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl ester

생성물 1

HCID 76568090racemic (2'S,3S,4'R)-6-chloro-2'-(3-chlorophenyl)-4'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione수율 6.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of racemic (2′S,3S,4′R)-6-chloro-2′-(3-chlorophenyl)-4′-(5-fluoro-2-methyl-phenyl)-2,3-dihydro-2,6′-dioxo-spiro[indole-3,3′-piperidine]-1-carboxylic acid ethyl ester prepared in example 145c (0.20 g, 0.31 mmol) in methanol (12 mL) was added NaOH (22 mg, 0.56 mmol). The mixture was stirred at room temperature for 0.5 h. The solvent was removed and the residue was partitioned between ethyl acetate and aqueous HCl solution (1 N). The aqueous layer was extracted with ethyl acetate. The organic layers were combined and then concentrated. The residue was purified with Prep-HPLC to give racemic (2′S,3S,4′R)-6-chloro-2′-(3-chlorophenyl)-4′-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (9 mg).

후처리

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and aqueous HCl solution (1 N)
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. concentrationconcentrated
  5. customThe residue was purified with Prep-HPLC

출처 및 근거

ORD 기록
ord-64613f409401470f9ecf19b1eae23369
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495007B2

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