Lawesson's reagent → [2-(4-nitrophenyl)-1-(S)-thiocarbamoylethyl]carbamic acid tert-butyl ester

HRID 424870Notes

Reaction equation

HRID 424870 reaction equation
[NH2:1][C:2](=O)[C@@H:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1COCC1>[C:17]([O:16][C:15](=[O:21])[NH:14][C@H:3]([C:2](=[S:32])[NH2:1])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 14134844(S)-tert-butyl 1-amino-3-(4-nitrophenyl)-1-oxopropan-2-ylcarbamate

Product 1

HCID 57943188[2-(4-nitrophenyl)-1-(S)-thiocarbamoylethyl]carbamic acid tert-butyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-tert-butyl 1-amino-3-(4-nitrophenyl)-1-oxopropa-2-ylcarbamate, 1, (0.400 g, 1.29 mmol) in THF (10 mL) is added Lawesson's reagent (0.262 g. 0.65 mmol). The reaction mixture is stirred for 3 hours and concentrated to a residue that is purified over silica to provide 0.350 g (83% yield) of the desired product. 1H NMR (300 MHz, CDCl3) δ 8.29 (s, 1H), 8.10 (d. J=8.4 Hz, 2H), 8.01 (s, 1H), 7.42 (d, J=8.4 Hz, 2H), 5.70 (d, J=7.2 Hz, 1H), 4.85 (d, J=7.2 Hz, 1H), 3.11-3.30 (m, 1H), 1.21 (s, 9H).

Workup

  1. concentrationconcentrated to a residue that
  2. customis purified over silica

Sources & evidence

ORD record
ord-676dc4340fb74d94920d401c9bc5dabb
Source dataset
uspto-grants-2012_01
Patent number
US08106078B2

Reaction notes

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