HCID 59366761, compound → HCID 59366638, compound

HRID 1923999Notes

Reaction equation

HRID 1923999 reaction equation
[CH3:1][N:2]([CH2:22][CH2:23][NH:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1)=[O:26])[C:3]([C@@H:5]([NH:14]C(=O)OC(C)(C)C)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]>Cl.C(OCC)C>[NH2:14][C@@H:5]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([N:2]([CH3:1])[CH2:22][CH2:23][NH:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][CH:28]=1)=[O:26])=[O:4]

Participants

4

Reactant 1

HCID 59366761HCID 59366761, compound

Product 1

HCID 59366638HCID 59366638, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of tert-butyl N-[(1S)-1-[methyl(2-{[4-(trifluoromethyl)phenyl]formamido}ethyl)carbamoyl]-3-phenylpropyl]carbamate CXXII (0.65 g, 1.23 mmol) in 1 M HCl in diethyl ether was stirred overnight. The solvent was evaporated under vacuum to give (2S)-2-amino-N-methyl-4-phenyl-N-(2-{[4-(trifluoromethyl)phenyl]formamido}ethyl)butanamide CXXIII as white crystals (0.46 g, 1.14 mmol, 93% yield). 1H NMR (DMSO-d6) 1.87-2.02 (m, 2H), 2.55-2.74 (m, 2H), 3.00 (s, 3H), 3.44-3.59 (m, 2H), 3.88-3.94 (m, 2H), 4.27 (brs, 1H), 7.18-7.28 (m, 6H), 7.71 (d, J=8 Hz, 2H), 7.95 (d, J=8 Hz, 2H), 8.29 (brs, 3H), 8.86-8.88 (m, 1H); ESIMS found for C21H24F3N3O2 m/z 408 (M+H).

Workup

  1. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-a3ce63d990d945d19a707937ce92b5b3
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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