Hydrogen Sulfide → HCID 54209529, compound

HRID 977215Notes

Reaction equation

HRID 977215 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH:12]([C:14]([NH:16][C@H:17]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])[O:11][C:10]2=[O:32])=[CH:5][CH:4]=1)#[N:2].N1C=CC=CC=1.[SH2:39]>C(N(CC)CC)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH:12]([C:14]([NH:16][C@H:17]([CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])=[O:15])[O:11][C:10]2=[O:32])=[CH:5][CH:4]=1)(=[S:39])[NH2:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 70116075tert-butyl (2R)-2-[3-(4-cyanophenyl)-2-oxo-5-oxazolidinylcarbonylamino]-3-phenylpropionate

Product 1

HCID 54209529HCID 54209529, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2.6 g of tert-butyl (2R)-2-[3-(4-cyanophenyl)-2-oxo-5-oxazolidinylcarbonylamino]-3-phenylpropionate [obtainable according to Example 8] are dissolved in a solvent mixture consisting of 30 ml of pyridine and 5 ml of triethylamine and the mixture is stirred for 1.5 h with ice cooling, with H2S gas being passed in continuously during this phase. The reaction mixture is subsequently stirred at room temperature for 24 h. Concentration by evaporation and customary workup give tert-butyl (2R)-2-[3-(4-thiocarbamoylphenyl)-2-oxo-5-oxazolidinylcarbonylamino]-3-phenylpropionate, m.p. 185°-186°.

Workup

  1. concentrationConcentration
  2. customby evaporation and customary workup

Sources & evidence

ORD record
ord-47f8fb613651463cab3890f6ad234aee
Source dataset
uspto-grants-1997_03
Patent number
US05614535

Reaction notes

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