Lawesson's reagent → tert-butyl (1R,3R,4S)-4-((benzyloxycarbonyl)amino)-3-carbamothioylcyclohexylcarbamate

HRID 2225311Notes

Reaction equation

HRID 2225311 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][C@H:13]1[C:26](=O)[NH2:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][C@H:13]1[C:26](=[S:38])[NH2:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86596980tert-butyl (1R,3R,4S)-4-((benzyloxycarbonyl)amino)-3-carbamoylcyclohexylcarbamate

Product 1

HCID 86596979tert-butyl (1R,3R,4S)-4-((benzyloxycarbonyl)amino)-3-carbamothioylcyclohexylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (1R,3R,4S)-4-((benzyloxycarbonyl)amino)-3-carbamoylcyclohexylcarbamate (4.8 g, 0.01 mol) in 50 ml of dry THF was added Lawesson's reagent (2.97 g, 0.007 mol) portionwise under nitrogen. After the completion of addition the reaction mixture was stirred for 5 h at RT. THF was removed and the crude product was dissolved in ethyl acetate. The organic layer was washed with 10% sodium hydroxide, water, brine and concentrated. The crude product was purified by recrystallization from pet-ether and ether mixture to give 3.5 g crude of tert-butyl (1R,3R,4S)-4-((benzyloxycarbonyl)amino)-3-carbamothioylcyclohexylcarbamate as a white solid.

Workup

  1. additionAfter the completion of addition the reaction mixture
  2. customTHF was removed
  3. dissolutionthe crude product was dissolved in ethyl acetate
  4. washThe organic layer was washed with 10% sodium hydroxide, water, brine
  5. concentrationconcentrated
  6. customThe crude product was purified by recrystallization from pet-ether and ether mixture

Sources & evidence

ORD record
ord-e3f26a8005fb458a8e208813b711db2e
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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