Acetic Acid → (2R,3R)-3-hydroxy-8-methyl-2-(4-methylphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1033477

Reaction equation

N[C@@H](C(O)=O)C(C)(C)C.[BH4-].[Na+].[CH3:12][C:13]1[CH:32]=[CH:31][C:16]2[NH:17][C:18](=[O:30])[C:19](=[O:29])[CH:20]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[S:21][C:15]=2[CH:14]=1.C(O)(=O)C>O1CCCC1>[OH:29][C@@H:19]1[C:18](=[O:30])[NH:17][C:16]2[CH:31]=[CH:32][C:13]([CH3:12])=[CH:14][C:15]=2[S:21][C@@H:20]1[C:22]1[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=1

Participants

Conditions

Temperature: -10 °C

Procedure

A mixture of D-tert-leucine (289 mg), sodium borohydride (76 mg) and tetrahydrofuran (15 ml) is refluxed under nitrogen atmosphere for three hours. The mixture is cooled to -10° C., and thereto is added a solution of 8-methyl-2-(4-methyl-phenyl)-1,5-benzothiazepine-3,4(2H,5H)-dione (297 mg) in tetrahydrofuran (3 ml). The mixture is stirred at -10° C. for 17 hours, and thereto is added acetic acid (600 mg). The mixture is evaporated under reduced pressure to remove the solvent. To the residue is added water (10 ml), and the precipitated crystal is collected by filtration, washed with water, and dried to give (2R,3R)-3-hydroxy-8-methyl-2-(4-methylphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (280 mg).

Workup

temperatureis refluxed under nitrogen atmosphere for three hours
customThe mixture is evaporated under reduced pressure
customto remove the solvent
additionTo the residue is added water (10 ml)
filtrationthe precipitated crystal is collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-3ef924ee835c48d98f8dd4a0dc73ee24
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05310904

Linked notes

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