Lawesson's reagent → 1,1-Dimethylethyl N-[(1S)-1-(aminothioxomethyl)-2-methylpropyl]carbamate

HRID 3141

Reaction equation

HRID 3141 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([NH2:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>C1COCC1>[C:1]([NH:8][C@H:9]([C:13](=[S:25])[NH2:15])[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 11241393Boc-L-valine amide

Product 1

HCID 110207761,1-Dimethylethyl N-[(1S)-1-(aminothioxomethyl)-2-methylpropyl]carbamateYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boc-valineamide (0.5 g) was stirred in dry THF at room temperature under argon. Lawesson's reagent (1.56 g, 0.6 eq) was added and the mixture was stirred overnight. The solvent was evaporated and the residue chromatographed (silica, 2.5% methanol/dichloromethane) to give the title compound as a white solid (0.373 g, 70%). NMR(CDCl3) δ 8.59 (1H, br s), 8.09 (1H, br s), 5.41 (1H, d (br)), 4.20 (1H, dd), 1.99 (1H, m), 1.39 (9H, s), 0.90 (6H, m).

Workup

  1. customThe solvent was evaporated
  2. customthe residue chromatographed (silica, 2.5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-0a45a609ac2e45e08721ea94db9274b3
Source dataset
uspto-grants-1998_03
Patent number
US05733882

Linked notes

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