Lawesson's reagent → HCID 90451724, compound

HRID 57406Notes

Reaction equation

HRID 57406 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@@H:8]([CH3:22])[C:9]([NH:11][NH:12][C:13](=O)[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=O)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:33]2)=CC=1>C1COCC1>[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]([C:9]1[S:33][C:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:12][N:11]=1)[CH3:22])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 90454299HCID 90454299, compound

Product 1

HCID 90451724HCID 90451724, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-tert-butyl(1-(2-(4-chlorobenzoyl)hydrazinyl)-1-oxopropan-2-yl)carbamate (1.0 g, 2.93 mmol) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (1.18 g, 2.93 mmol, 1.0 equiv) in THF (29 mL) was heated at reflux for 2 hours. The reaction wash then cooled to room temperature and filtered through a pad of celite, using THF to wash through. The filtrate was concentrated in vacuo. Silica gel column chromatography (EtOAc/Heptane, 0 to 30%) provided (S)-tert-butyl(1-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)ethyl)carbamate (0.600 g, light green solid) in 60% yield. 1H NMR (400 MHz, CDCl3) δ 7.89 (d, J=8.5 Hz, 2H), 7.46 (d, J=8.5 Hz, 2H), 5.23 (m, 1H), 1.72 (d, J=6.5 Hz, 3H), 1.48 (s, 9H). MS m/z 340.1 (M+H)+; Rt-0.99 min.

Workup

  1. temperatureat reflux for 2 hours
  2. washThe reaction wash
  3. filtrationfiltered through a pad of celite
  4. washto wash through
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-dac74217dbdd447a853645e7562eb931
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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