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 133128

반응식

HRID 133128 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-lysine

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 702Ethanol용매

실험 절차

A mixture of benzyl (5S)—N2,N2-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-nitro-D-norleucinate from Step C (15.5 g, 26.8 mmol) and 10% Pd/C (12.0 g) in EtOH (175 mL), was hydrogenated at 55 psi for 18 h. An additional portion of 10% Pd/C (4.0 g) was added and the reaction mixture was hydrogenated at 55 psi for a further 18 h. The reaction mixture was filtered through Celite, washing with EtOH, and the filtrate was concentrated in vacuo to afford the title compound. MS: m/z=459 (M+1).

후처리

  1. waitthe reaction mixture was hydrogenated at 55 psi for a further 18 h
  2. filtrationThe reaction mixture was filtered through Celite
  3. washwashing with EtOH
  4. concentrationthe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-511bfca82ab94a3c96737d18975c786b
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390798B2

연결된 노트

불러오는 중…