Lawesson's reagent → 5-(Tert-butoxycarbonylamino-methyl)-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester

HRID 2175413Notes

Reaction equation

HRID 2175413 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][NH:13][C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:30][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][N:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 10108216Ethyl (N-{2-[(tert-butoxy)carbonylamino]acetylamino}carbamoyl)formate

Product 1

HCID 867295725-(Tert-butoxycarbonylamino-methyl)-[1,3,4]thiadiazole-2-carboxylic acid ethyl esterYield 261.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of ethyl 2-(2-(2-(tert-butoxycarbonylamino)acetyl) hydrazinyl)-2-oxoacetate (9-4) (228 mg, 0.6913 mmol) in THF (10 mL) was added lawesson's reagent (354 mg, 0.8669 mmol). The solution was heated to reflux for 3 h. Then solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel with the eluant (PE/EA/NEt3=10/1/1%; 5/1/1%; 2/1/1%). The yellow solid was obtained as the product (520 mg, 69%). 1H NMR (500 MHz, CDCl3) δ 5.31 (br, 1H), 4.76 (d, J=6.1 Hz, 2H), 4.51 (d, J=14, 7.1 Hz, 2H), 1.60-1.39 (m, 12H); LRMS (ESI) calculated M+H for C11H18N3O4S: 288.3; Found: 288.1.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 3 h
  3. customThen solvent was evaporated under reduced pressure
  4. customthe residue was purified by chromatography on silica gel with the eluant (PE/EA/NEt3=10/1/1%; 5/1/1%; 2/1/1%)

Sources & evidence

ORD record
ord-322551a325304b1dab48274c9133c7ef
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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