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

HRID 2409120Notes

Reaction equation

HRID 2409120 reaction equation
CO[C:3](=[O:19])[CH2:4][C@:5]([NH2:18])([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[CH2:6][CH2:7][CH3:8].[CH3:20][NH:21][C:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=S>>[C:27]([O:26][C:25](=[O:31])[NH:24][C:22]1[N:21]([CH3:20])[C:3](=[O:19])[CH2:4][C@:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)([CH2:6][CH2:7][CH3:8])[N:18]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

3

Reactant 2

HCID 57496573tert-butyl N-(methylcarbamothioyl)carbamateHCID 66727741(S)-3-amino-3-(3-nitro-phenyl)-hexanoic acid methyl ester

Product 1

HCID 57497152[(S)-1-methyl-4-(3-nitro-phenyl)-6-oxo-4-propyl-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

Procedure

Starting from (S)-3-amino-3-(3-nitro-phenyl)-hexanoic acid methyl ester and tert-butyl [(methylamino)carbonothioyl]carbamate, the product [(S)-1-methyl-4-(3-nitro-phenyl)-6-oxo-4-propyl-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester was obtained as an amorphous solid. MS (ESI): m/z=389.3 [M−H]−.

Sources & evidence

ORD record
ord-ff12a254a98747bdb900c860df7a5f6e
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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