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Water → (S)-2-Amino-6,6,6-trifluoro-5-phenyl-hexanoic acid methyl ester

HRID 1026110
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HRID 1026110 반응식
C([C@@H]1C(OC)=[N:8][C@@H:7]([CH2:12][CH2:13][CH:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([F:18])([F:17])[F:16])[C:6]([O:25][CH3:26])=N1)(C)C.O.FC(F)(F)C(O)=[O:31].[Cl-].[NH4+]>C(#N)C>[CH3:26][O:25][C:6](=[O:31])[C@@H:7]([NH2:8])[CH2:12][CH2:13][CH:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]([F:18])([F:17])[F:16]
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6

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HCID 962WaterHCID 6422Trifluoroacetic acidHCID 25517Ammonium ChlorideHCID 67177689(2R,5S)-2-Isopropyl-3,6-dimethoxy-5-(4,4,4-trifluoro-3-phenyl-butyl)-2,5-dihydro-pyrazine

생성물 1

HCID 67177271(S)-2-Amino-6,6,6-trifluoro-5-phenyl-hexanoic acid methyl ester

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
40 °C

실험 절차

To a solution of (2R,5S)-2-isopropyl-3,6-dimethoxy-5-(4,4,4-trifluoro-3-phenyl-butyl)-2,5-dihydro-pyrazine (1.86 g) in acetonitrile (18 ml) were added water (7 ml) and trifluoroacetic acid (3.8 ml). The mixture was stirred overnight at 40° C. Saturated ammonium chloride solution was added and the mixture was extracted with dichloromethane three times. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (SiO2, EtOAc/MeOH=98:2 to yield a light yellow solid, (0.98 g, 71%); MS (ISP): 276.1 ((M+H)+).

후처리

  1. extractionthe mixture was extracted with dichloromethane three times
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography (SiO2, EtOAc/MeOH=98:2
  6. customto yield a light yellow solid, (0.98 g, 71%)

출처 및 근거

ORD 기록
ord-751cfc272a7e4db5958ecb0c8196f6e2
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08729113B2

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