Triethylamine → 5-(S)-Thioacetamidomethyl-3-[4'-(tert-butoxy)carbonyl-3'-fluorophenyl]oxazo-lidine-2-one

HRID 2305649Notes

Reaction equation

HRID 2305649 reaction equation
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:11]([F:22])[CH:10]=2)[CH2:4]1.C(N(CC)CC)C.[C:30](SCC)(=[S:32])[CH3:31]>CN(C=O)C.C(OCC)(=O)C>[C:30]([NH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])=[C:11]([F:22])[CH:10]=2)[CH2:4]1)(=[S:32])[CH3:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 70093Ethyl dithioacetateHCID 229662025-(S)-Aminomethyl-3-[4'-tert-butoxycarbonyl-3'-fluorophenyl]-oxazolidine-2-one

Product 1

HCID 98206105-(S)-Thioacetamidomethyl-3-[4'-(tert-butoxy)carbonyl-3'-fluorophenyl]oxazo-lidine-2-oneYield 84.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(S)-aminomethyl-3-[4′-(tert-butoxy)carbonyl-3′-fluorophenyl]-oxazolidine-2-one (3.00 g, 9.66 mmol), triethylamine (1.35 ml, 19.3 mmol), and ethyl dithioacetate (1.22 ml, 10.6 mmol) in DMF (8 mL) was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate (50 ml), washed with 3% aqueous citric acid (3×30 mL), saturated aqueous sodium bicarbonate (30 mL), brine, and dried (MgSO4). Evaporation afforded the product as a white solid (3.00 g, 84%). MS (m/z): [M+H]+=369.

Workup

  1. washwashed with 3% aqueous citric acid (3×30 mL), saturated aqueous sodium bicarbonate (30 mL), brine
  2. dry with materialdried (MgSO4)
  3. customEvaporation

Sources & evidence

ORD record
ord-893d0132083e466aaca063f94079a8bd
Source dataset
uspto-grants-2002_08
Patent number
US06441005B1

Reaction notes

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