tert-butyl N-(methylcarbamothioyl)carbamate → [(S)-4-ethyl-1-methyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

HRID 1255783Notes

Reaction equation

HRID 1255783 reaction equation
CO[C:3](=[O:18])[CH2:4][C@:5]([NH2:17])([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1)[CH2:6][CH3:7].[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]([CH2:6][CH3:7])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)[N:17]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 57496573tert-butyl N-(methylcarbamothioyl)carbamateHCID 66644170(S)-3-amino-3-(3-nitro-phenyl)-pentanoic acid methyl ester

Product 1

HCID 57496581[(S)-4-ethyl-1-methyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

Procedure

Starting from (S)-3-amino-3-(3-nitro-phenyl)-pentanoic acid methyl ester (1.2 mmole) and tert-butyl [(methylamino)carbonothioyl]carbamate, the product [(S)-4-ethyl-1-methyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (372 mg) was obtained as white solid. MS (ESI): m/z=375.4 [ M−H]−.

Sources & evidence

ORD record
ord-7b2a4036f3cc4a89a25bf3b459d105a2
Source dataset
uspto-grants-2013_06
Patent number
US08461160B2

Reaction notes

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