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

HRID 885160Notes

Reaction equation

HRID 885160 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

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)+).

Workup

  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%)

Sources & evidence

ORD record
ord-ac80e09f1b274dc0bb6f770ea109bea8
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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