Ethanol → Sacubitril N-Boc Ester

HRID 2174881노트

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HRID 2174881 반응식
[CH2:1]([O:3][C:4](=[O:30])[C:5](=[CH2:29])[CH2:6][C@H:7]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH3:2].C(O)C.[H][H]>[Pd].C(N(CC)CC)C>[CH2:1]([O:3][C:4](=[O:30])[CH:5]([CH3:29])[CH2:6][CH:7]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH3:2]

참가 물질

6

반응물 3

HCID 702EthanolHCID 66958146(R)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylenepentanoic acid ethyl ester2회HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 58160380Sacubitril N-Boc Ester

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8471Triethylamine용매

실험 절차

500 mg (R)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylenepentanoic acid ethyl ester (2-a, R1=Boc, R2=H, R3=CO2Et) is added to ethanol (5 ml) at ambient temperature. Triethylamine (170 μl) is then added to the mixture. 50 mg Palladium on carbon (10%, 50% water-wet, Degussa E101 NE/W) is then added. Hydrogen gas at ambient pressure is applied to the mixture. The mixture is then stirred overnight at ambient temperature and pressure. The mixture is then filtered and concentrated under reduced pressure to afford 2R,4S)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid ethyl ester (1-a, R1=Boc, R2=H, R3=CO2Et) and (2S,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid ethyl ester (1-b, R1=Boc, R2=H, R3=CO2Et). Spectroscopic data as in Example 63. Ratio of diastereomers 70:30 (1-a, R1=Boc, R2=H, R3=CO2Et:1-b, R1=Boc, R2=H, R3=CO2Et) as determined by hplc (hplc method as in Example 65)

후처리

  1. filtrationThe mixture is then filtered
  2. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2bca07c499ec4e9ea7e6ad2442362867
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09061973B2

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