Water → 2-(3-(3-((S)-2-Amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydropyrimidin-4-yl)-4-fluorophenylamino)cyclopentyl)acetic acid

HRID 2409184노트

반응식

HRID 2409184 반응식
C[O:2][C:3](=[O:30])[CH2:4][CH:5]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C@:18]3([CH3:29])[C:23]([CH3:25])([CH3:24])[C:22](=[O:26])[N:21]([CH3:27])[C:20]([NH2:28])=[N:19]3)[CH:12]=2)[CH2:6]1.O.[Li+].[OH-]>C1COCC1.CO>[NH2:28][C:20]1[N:21]([CH3:27])[C:22](=[O:26])[C:23]([CH3:24])([CH3:25])[C@:18]([C:13]2[CH:12]=[C:11]([NH:10][CH:7]3[CH2:8][CH2:9][CH:5]([CH2:4][C:3]([OH:30])=[O:2])[CH2:6]3)[CH:16]=[CH:15][C:14]=2[F:17])([CH3:29])[N:19]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57516115{3-[3-((S)-2-Amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-4-yl)-4-fluoro-phenylamino]-cyclopentyl}-acetic acid methyl ester

생성물 1

HCID 575161222-(3-(3-((S)-2-Amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydropyrimidin-4-yl)-4-fluorophenylamino)cyclopentyl)acetic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of {3-[3-((S)-2-amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-4-yl)-4-fluoro-phenylamino]-cyclopentyl}-acetic acid methyl ester (example 95, 0.05 mmol) in THF (1 ml), MeOH (0.3 ml), and H2O (0.3 ml) was added LiOH (1N, 0.1 mmol) and the reaction mixture was stirred at room temperature for 4 h. The mixture was concentrated in vacuo and the residue diluted with aqueous HCl (0.5N) until pH=5 and EtOAc. The white solid which precipitate was filtered off, washed with H2O and dried. The organic phase was dried over Na2SO4 and evaporated to yield a white solid. The combined solid material was triturated with a mixture of dichloromethane and MeOH (10:1), filtered and the filtrate was concentrated in vacuo to yield a mixture of isomers of the title compound as a white solid. MS (ESI): m/z=405.5 [M+H]+.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue diluted with aqueous HCl (0.5N) until pH=5 and EtOAc
  3. filtrationThe white solid which precipitate was filtered off
  4. washwashed with H2O
  5. customdried
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customevaporated
  8. customto yield a white solid
  9. customThe combined solid material was triturated with a mixture of dichloromethane and MeOH (10:1)
  10. filtrationfiltered
  11. concentrationthe filtrate was concentrated in vacuo
  12. customto yield

출처 및 근거

ORD 기록
ord-c61289ff23544a5fa89e0a3c12b2b8f7
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815881B2

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