Lawesson's reagent → (S)-tert-Butyl 1-amino-3-cyclopropyl-1-thioxopropan-2-ylcarbamate

HRID 632062Notes

Reaction equation

[NH2:1][C:2](=O)[C@@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH:5]1[CH2:7][CH2:6]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1(C)C=CC=CC=1>[NH2:1][C:2](=[S:26])[C@@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH:5]1[CH2:7][CH2:6]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (S)-tert-butyl 1-amino-3-cyclopropyl-1-oxopropan-2-ylcarbamate (Example 38 a, 6.7 g, 29 mmol) and Lawesson's reagent (CAN 19172-47-5, 6.06 g, 15 mmol) in toluene (60 mL) was stirred at 90° C. for 2.5 h. After removal of the solvent in vacuo, the residue was purified by column chromatography (silica gel, 100 g, eluting with 5% methanol in ethyl acetate) to yield the title compound (5.1 g, 71%) as yellow solid; MS: m/e=267.1 [M+Na]+

Workup

customAfter removal of the solvent in vacuo
customthe residue was purified by column chromatography (silica gel, 100 g, eluting with 5% methanol in ethyl acetate)

Sources & evidence

ORD record: ord-ccd5beb50a8f492c91b8751e87cb9c16
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321727B2

Reaction notes

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