(s)-2-Mercaptosuccinic acid → 2-((5S)-2-(3-fluoro-2-(3,3-difluoropyrrolidin-1-yl)phenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid

HRID 1695948

반응식

HRID 1695948 반응식
[F:1][C:2]1([F:22])[CH2:6][CH2:5][N:4]([C:7]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:8]=2[CH:9]=[N:10][CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:3]1.[SH:23][C@@H:24]([CH2:28][C:29]([OH:31])=[O:30])[C:25](O)=[O:26]>C1(C)C=CC=CC=1>[F:21][C:20]1[C:7]([N:4]2[CH2:5][CH2:6][C:2]([F:1])([F:22])[CH2:3]2)=[C:8]([CH:9]2[N:10]([CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:25](=[O:26])[C@H:24]([CH2:28][C:29]([OH:31])=[O:30])[S:23]2)[CH:17]=[CH:18][CH:19]=1

참가 물질

4

반응물 2

HCID 3246154(s)-2-Mercaptosuccinic acidHCID 57774377N-(2-(3,3-Difluoropyrrolidin-1-yl)-3-fluorobenzylidene)-3,3-dimethylbutan-1-amine

생성물 1

HCID 577744612-((5S)-2-(3-fluoro-2-(3,3-difluoropyrrolidin-1-yl)phenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

N-(2-(3,3-Difluoropyrrolidin-1-yl)-3-fluorobenzylidene)-3,3-dimethylbutan-1-amine (400.2 mg, 1.281 mmol) was taken in toluene and (S)-2-mercaptosuccinic acid (192.3 mg, 1.281 mmol) was added. The reaction mixture was refluxed overnight with a Dean Stark trap to remove the water. Then the reaction mixture was concentrated, triturated with ether and dried overnight to give 2-((5S)-2-(3-fluoro-2-(3,3-difluoropyrrolidin-1-yl)phenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid which was used directly in the next step. The product was identified by LC/MS. LC/MS: m/z=445.5M+1.

후처리

  1. temperatureThe reaction mixture was refluxed overnight with a Dean Stark trap
  2. customto remove the water
  3. concentrationThen the reaction mixture was concentrated
  4. customtriturated with ether
  5. customdried overnight

출처 및 근거

ORD 기록
ord-8f27f72a01754679a908aef6a39b539c
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163737B2

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