Tert-butyl [(benzylamino)carbonothioyl]carbamate → [(S)-1-benzyl-4-methyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

HRID 1255785Notes

Reaction equation

HRID 1255785 reaction equation
CO[C:3](=[O:17])[CH2:4][C@:5]([NH2:16])([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH3:6].[CH2:18]([NH:25][C:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=S)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:31]([O:30][C:29](=[O:35])[NH:28][C:26]1[N:25]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:3](=[O:17])[CH2:4][C@@:5]([CH3:6])([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=2)[N:16]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

3

Reactant 2

HCID 57496577Tert-butyl [(benzylamino)carbonothioyl]carbamateHCID 57505082(S)-3-amino-3-(3-nitro-phenyl)-butyric acid methyl ester

Product 1

HCID 57496578[(S)-1-benzyl-4-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)-butyric acid methyl ester (0.42 mmole) and tert-butyl [(benzylamino)carbonothioyl]carbamate, the product [(S)-1-benzyl-4-methyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (165 mg) was obtained as a white solid. MS (ESI): m/z=439.3 [ M+H]+.

Sources & evidence

ORD record
ord-fed0d93bc5394f329dfb84a5c3dfcc56
Source dataset
uspto-grants-2013_06
Patent number
US08461160B2

Reaction notes

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