Ethyl Acetate → HCID 86730170, compound

HRID 1850134Notes

Reaction equation

HRID 1850134 reaction equation
[C:1]([NH:9][NH:10][C:11](=O)[C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1.C(OCC)(=O)C>CCCCCCC>[C:2]1([C:1]2[S:32][C:11]([C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])=[N:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 86730169HCID 86730169, compound

Product 1

HCID 86730170HCID 86730170, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

To a solution of (S)-tert-butyl (1-(2-benzoylhydrazinyl)-1-oxopropan-2-yl)carbamate (155 mg, 0.5 mmol, 1.0 equv. in 5 ml of THF) was added Lawesson's reagent (36.4 mg, 0.5 mmol, 1.0 equv.) the reaction mixture was stirred at reflux for 3 hours, the reaction mixture was filtered and the solvent was removed to yield the crude product. Silica gel column chromatography (ethyl acetate in heptane 10 to 50%) to provide (S)-tert-butyl (1-(5-phenyl-1,3,4-thiadiazol-2-yl)ethyl)carbamate (114.6 mg, white solid) in 70.7% yield. 1H NMR (400 MHz, CD2Cl2) δ 7.94-7.72 (m, 2H), 7.52-7.26 (m, 3H), 5.59 (b, 1H), 5.11 (b, 1H), 1.57 (d, J=7.0 Hz, 3H), 1.34 (s, 9H).

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationthe reaction mixture was filtered
  3. customthe solvent was removed
  4. customto yield the crude product

Sources & evidence

ORD record
ord-2b1cae2bf37a4bd78e5e32de0f36618c
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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