Benzyl mercaptan → 3-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[(benzylthio)methyl]-tetrahydrofuran

HRID 413368Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]([CH2:24][CH:25]3[O:27][CH2:26]3)[C:20](OC)=[O:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].CCN(CC)CC.[CH2:40]([SH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([NH:18][CH:19]3[CH2:24][CH:25]([CH2:26][S:47][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[O:27][C:20]3=[O:21])(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 2-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoate 1d (0.5 g, 1.28 mmol) in benzene (3 mL), NaHCO3 (0.32 g, 3.84 mmol) and Et3N (0.23 mL, 1.6 mmol) at room temperature is added slowly benzyl mercaptan (0.62 mL, 4.99 mmol). The reaction mixture is heated at 70° C. for 3 h, and stirred two days at room temperature. The resulting mixture is diluted with water, and then the mixture is extracted three times with EtOAc. The combined EtOAc layer is washed with water, brine, dried over MgSO4 and concentrated to an oil which is purified by column chromatography eluting with hexane/EtOAc (4:1) to give the desired product.

Workup

extractionthe mixture is extracted three times with EtOAc
washThe combined EtOAc layer is washed with water, brine
dry with materialdried over MgSO4
concentrationconcentrated to an oil which
customis purified by column chromatography
washeluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record: ord-58e6714a78dc4ad880b5621a36a87da4
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566381B1

Reaction notes

Loading…