Lawesson's reagent → HCID 86668964, compound

HRID 877369Notes

Reaction equation

HRID 877369 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([O:27][C:28]([NH:30][C@@H:31]([C:33]([NH:35][CH2:36][C:37](=O)[CH3:38])=O)[CH3:32])=[O:29])([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[CH3:38][C:37]1[S:10][C:33]([C@H:31]([NH:30][C:28](=[O:29])[O:27][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:32])=[N:35][CH:36]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86668963HCID 86668963, compound

Product 1

HCID 86668964HCID 86668964, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lawesson's Reagent (14 g, 35 mmol) was added to a solution of N2-(tert-butoxycarbonyl)-N-(2-oxopropyl)-D-alaninamide (8.5 g, 34.5 mmol) in THF (300 ml), and the resulting mixture was refluxed for 6 h. After concentration, the residue was purified by column, and 2.8 g of tert-butyl [(1R)-1-(5-methyl-1,3-thiazol-2-yl)ethyl]carbamate was obtained as solid (35%). 1H-NMR CDCl3 δ 7.31 (s, 1H), 5.24 (br, 1H), 5.00 (m, 1H), 2.42 (s, 3H), 1.55 (d, J=6.8 Hz, 3H), 1.44 (s, 9H) ES-MS [M+1]+: 243.14.

Workup

  1. temperaturethe resulting mixture was refluxed for 6 h
  2. concentrationAfter concentration
  3. customthe residue was purified by column

Sources & evidence

ORD record
ord-41b5f54d65784f58b90c9c37f31b1cf8
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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