Lawesson's reagent → HCID 58109130, compound

HRID 2037696Notes

Reaction equation

HRID 2037696 reaction equation
[C:1]([NH:4][NH:5][C:6](=O)[CH2:7][C@@:8]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)[CH3:16])[CH2:10][CH2:9]1)(=O)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>C1COCC1>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([C@@H:15]([N:11]2[CH2:10][CH2:9][C@:8]([CH2:7][C:6]3[S:40][C:1]([CH3:2])=[N:4][N:5]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:13][C:12]2=[O:14])[CH3:16])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58109300HCID 58109300, compound

Product 1

HCID 58109130HCID 58109130, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N′-acetyl-2-((S)-3-((S)-1-(4-bromophenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)acetohydrazide (50 mg, 0.105 mmol) in anhydrous THF (2 mL) was added Lawesson's Reagent (50 mg, 0.126 mmol) at rt. The mixture was heated to reflux for 3 h. The mixture was concentrated to give the crude product, which was purified by preparative TLC to give (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-((5-methyl-1,3,4-thiadiazol-2-yl)methyl)-6-phenyl-1,3-oxazinan-2-one (10 mg, 20%). 1H NMR (400 MHz, CDCl3): δ=1.39 (d, 3H), 2.02 (m, 1H), 2.22 (m, 1H), 2.39 (m, 1H), 2.69 (s, 3H), 2.81 (m, 1H), 3.58 (m, 1H), 5.52 (q, 1H), 6.66 (m, 2H), 7.16 (m, 2H), 7.21 (m, 2H), 7.32 (m, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. concentrationThe mixture was concentrated
  4. customto give the crude product, which
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-be084e34b9fb472f9f5dcd06112f1949
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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