Lawesson's reagent → tert-butyl [(1R)-2-amino-1-methyl-2-thioxoethyl]carbamate

HRID 1099097

Reaction equation

HRID 1099097 reaction equation
COC1C=CC(P2(=S)SP(C3C=CC(OC)=CC=3)(=S)[S:10]2)=CC=1.[C:23]([O:27][C:28](=[O:35])[NH:29][C@H:30]([CH3:34])[C:31]([NH2:33])=O)([CH3:26])([CH3:25])[CH3:24]>COCCOC>[C:23]([O:27][C:28](=[O:35])[NH:29][C@H:30]([CH3:34])[C:31]([NH2:33])=[S:10])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 7015296Boc-D-Ala-NH2

Product 1

HCID 5324342tert-butyl [(1R)-2-amino-1-methyl-2-thioxoethyl]carbamateYield 203.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2,4-Bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane (1.6 g, 0.0038 mol) was added to a solution of tert-butyl[(1R)-2-amino-1-methyl-2-oxoethyl]carbamate (1.45 g, 0.00770 mol) in 1,2-dimethoxyethane (40 mL). The resulting suspension was stirred at RT for 5 h. After removal of solvent the residue was taken up into ethyl acetate. It was washed with 0.1 N NaOH solution, water, brine; dried over Na2SO4. After filtration the filtrate was concentrated to yield 1.58 g of the product. (yield: ˜100%).

Workup

  1. customAfter removal of solvent the residue
  2. washIt was washed with 0.1 N NaOH solution, water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration the filtrate
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-2367931cdfd842fa98bc713e4691fa14
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Linked notes

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