benzyl (5S)-N,N-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate → (5S)-N2,N2-Bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-D-lysine

HRID 14391

반응식

HRID 14391 반응식
[C:1]([O:5][C:6]([N:8]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@@H:9]([C:25]([O:27]CC1C=CC=CC=1)=[O:26])[CH2:10][CH2:11][C@@H:12]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[F:24])[CH2:13][N+:14]([O-])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:38]([O:37][C:35]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@@H:9]([C:25]([OH:27])=[O:26])[CH2:10][CH2:11][C@@H:12]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[F:24])[CH2:13][NH2:14])=[O:36])([CH3:41])([CH3:40])[CH3:39]

참가 물질

4

반응물 1

HCID 25034375benzyl (5S)-N,N-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate

생성물 1

HCID 67526479(5S)-N2,N2-Bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-D-lysine수율 97.7%

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 702Ethanol용매

실험 절차

A solution of benzyl (5S)-N,N-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate (15.5 g, 26.8 mmol) and 10% Pd/C (12.0 g) in EtOH (175 mL, SureSeal from Aldrich), was hydrogenated at 55 psi overnight. After 18 h, another 4 g of 10% Pd/C was added and the reaction hydrogenated at 55 psi for another 18 h. The reaction was filtered through Celite with more EtOH and concentrated to afford the title compound (12.0 g). MS 459.2 (M+1).

후처리

  1. customwas hydrogenated at 55 psi overnight
  2. customthe reaction hydrogenated at 55 psi for another 18 h
  3. filtrationThe reaction was filtered through Celite with more EtOH
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-714a45d75f1a47ea96f79fcebb22b012
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732438B2

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