L-Isoleucine → 3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-
Reaction equation
N[C@H](C(O)=O)[C@H](CC)C.[BH4-].[Na+].O1CCCC1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[C:31](=[O:32])[C:30](=[O:33])[NH:29][C:28]3[CH:34]=[CH:35][CH:36]=[CH:37][C:27]=3[S:26]2)=[CH:21][CH:20]=1>C(O)(=O)C>[OH:32][C@H:31]1[C:30](=[O:33])[NH:29][C:28]2[CH:34]=[CH:35][CH:36]=[CH:37][C:27]=2[S:26][C@H:25]1[C:22]1[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A mixture of L-isoleucine (289 mg), sodium borohydride (76 mg) and tetrahydrofuran (15 ml) is refluxed under nitrogen atmosphere for three hours. The mixture is cooled to -20° C., and thereto is added 2-(4-methoxyphenyl)-1,5-benzothiazepine-3,4(2H,5H)-dione (299 mg), and the mixture is stirred at the same temperature for 20 hours. To the reaction solution is added acetic acid (600 mg), and the mixture is stirred for two hours, and then evaporated under reduced pressure to remove the solvent. Water is added to the residue, and the precipitated crystal is collected by filtration, washed with water, and dried to give (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (263 mg).
Workup
- temperatureis refluxed under nitrogen atmosphere for three hours
- stirringthe mixture is stirred for two hours
- customevaporated under reduced pressure
- customto remove the solvent
- additionWater is added to the residue
- filtrationthe precipitated crystal is collected by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-cbdbfba4bb6a453d83298a7637b66a62
- Source dataset
- uspto-grants-1994_05
- Patent number
- US05310904
Reaction notes
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