methyl (S)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionate → (3R)-3-(cycloheptylmethyl)-6-(3,5-difluorophenyl)piperazin-2-one

HRID 1615768노트

반응식

HRID 1615768 반응식
C([N:8]([CH2:22][C:23]([C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=1)=[N:24]O)[C@H:9]([CH2:14][CH:15]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:10](OC)=[O:11])C1C=CC=CC=1.C(N(CC(C1C=C(F)C=C(F)C=1)=NO)[C@@H](CC1CCCCCC1)C(OC)=O)C1C=CC=CC=1.[H][H]>[Pd].CO>[CH:15]1([CH2:14][C@H:9]2[NH:8][CH2:22][CH:23]([C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=3)[NH:24][C:10]2=[O:11])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

6

반응물 3

HCID 86668536methyl (S)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionateHCID 86668541methyl (R)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 68760174(3R)-3-(cycloheptylmethyl)-6-(3,5-difluorophenyl)piperazin-2-one

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

Under a hydrogen atmosphere 5.5 g (12.0 mmol) methyl (R)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionate (this compound may be prepared analogously to the synthesis of methyl (S)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionate described herein using the corresponding (R)-configured starting component) and 0.70 g palladium on charcoal (10%) were hydrogenated in 30 ml of methanol for 3 days at 50° C. to 60° C. and 3 bar hydrogen pressure. After elimination of the catalyst the filtrate was concentrated by rotary evaporation. Purification was carried out by flash chromatography.

후처리

  1. concentrationAfter elimination of the catalyst the filtrate was concentrated by rotary evaporation
  2. customPurification

출처 및 근거

ORD 기록
ord-c5f5cf3a4e9f477a80283d4dcbac531a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765763B2

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