Lawesson's reagent → Carbamic acid, (2-amino-1,1-dimethyl-2-thioxoethyl)-, 1,1-dimethylethyl ester

HRID 1671244Notes

Reaction equation

HRID 1671244 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C:9]([CH3:14])([C:11]([NH2:13])=O)[CH3:10])=[O:7])([CH3:4])[CH3:3].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>O1CCCC1>[NH2:13][C:11](=[S:24])[C:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:14])[CH3:10]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 11287144tert-Butyl (1-amino-2-methyl-1-oxopropan-2-yl)carbamate

Product 1

HCID 15186362Carbamic acid, (2-amino-1,1-dimethyl-2-thioxoethyl)-, 1,1-dimethylethyl esterYield 48.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N2-{[(1,1-dimethylethyl)oxy]carbonyl}-2-methylalaninamide (3.87 g, 19.13 mmol), Lawesson's reagent (7.74 g, 19.13 mmol) and tetrahydrofuran (THF) (100 mL) was heated to 50° C. for 3 hours. The reaction was concentrated, added 150 cc of EtOAc and washed with sat'd NaHCO3 (3×100 cc), water and brine. The EtOAc layer was concentrated and the residue was purified via chromatography on silica gel eluted Hex to 1:1 Hex/EtOAc to obtain the title compound (2.04 g, 48% yield).

Workup

  1. concentrationThe reaction was concentrated
  2. additionadded 150 cc of EtOAc
  3. washwashed with sat'd NaHCO3 (3×100 cc), water and brine
  4. concentrationThe EtOAc layer was concentrated
  5. customthe residue was purified via chromatography on silica gel eluted Hex to 1:1 Hex/EtOAc

Sources & evidence

ORD record
ord-08a0bf909b8d426785110f3b8af266ca
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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