Dimethylformamide → tert-Butyl 3-(2-Methylpropyl)-2-oxo-1-(2-phenylethyl)-alpha-[2-(2-thienylthio)ethyl]-3-pyrrolidineacetate

HRID 727534Notes

Reaction equation

[H-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[SH:8].CN(C=O)C.CS(O[CH2:19][CH2:20][CH:21]([C:29]1([CH2:43][CH:44]([CH3:46])[CH3:45])[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]1=[O:42])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])(=O)=O>C1COCC1>[CH3:45][CH:44]([CH3:46])[CH2:43][C:29]1([CH:21]([CH2:20][CH2:19][S:8][C:4]2[S:3][CH:7]=[CH:6][CH:5]=2)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:30]1=[O:42]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60%, 41 mg, 1.0 mmol) is added to a solution of thiophenethiol (118 mg, 1.02 mmol), THF (25 mL) and DMF (25 mL) at 0° C. The mixture is stirred for 30 minutes at 0° C. and a solution of tert-butyl α-[2-(methanesulfonyloxy)ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (490 mg, 1.02 mmol) in THF (15 mL) is added. The solution is allowed to warm slowly and is stirred at room temperature overnight. Concentration, aqueous workup (EtOAc, MgSO4), and purification by flash chromatography (25% EtOAc/hexane) gives 361 mg (71%) of title compound as a colorless oil.

Workup

temperatureto warm slowly
stirringis stirred at room temperature overnight
concentrationConcentration, aqueous workup (EtOAc, MgSO4), and purification by flash chromatography (25% EtOAc/hexane)

Sources & evidence

ORD record: ord-4599f6bbcc144aa39894b465bd404a45
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712300

Reaction notes

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