tert-butyl N-(methylcarbamothioyl)carbamate → [(S)-4-(2-fluoro-5-nitro-phenyl)-1,4-dimethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

HRID 1255784Notes

Reaction equation

HRID 1255784 reaction equation
CO[C:3](=[O:18])[CH2:4][C@:5]([NH2:17])([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[F:16])[CH3:6].[CH3:19][NH:20][C:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=S>>[C:26]([O:25][C:24](=[O:30])[NH:23][C:21]1[N:20]([CH3:19])[C:3](=[O:18])[CH2:4][C@:5]([C:7]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=2[F:16])([CH3:6])[N:17]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 57496573tert-butyl N-(methylcarbamothioyl)carbamateHCID 57505083(S)-Methyl 3-Amino-3-(2-fluoro-5-nitrophenyl)butanoate

Product 1

HCID 57501006[(S)-4-(2-fluoro-5-nitro-phenyl)-1,4-dimethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

Procedure

Starting from (S)-3-amino-3-(2-fluoro-5-nitro-phenyl)-butyric acid methyl ester (14.8 mmole) and tert-butyl [(methylamino)carbonothioyl]carbamate, the product [(S)-4-(2-fluoro-5-nitro-phenyl)-1,4-dimethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (3.13 g) was obtained as pale yellow foam. MS (ESI): m/z=381.2 [ M+H]+.

Sources & evidence

ORD record
ord-42515884b6d343dea2f67aa6e692880c
Source dataset
uspto-grants-2013_06
Patent number
US08461160B2

Reaction notes

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