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

HRID 1033477

反応式

HRID 1033477 の反応式
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

参加物

6

反応物 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 6950340D-tert-leucineHCID 190261378-methyl-2-(4-methyl-phenyl)-1,5-benzothiazepine-3,4(2H,5H)-dione

生成物 1

HCID 10566075(2R,3R)-3-hydroxy-8-methyl-2-(4-methylphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one収率 93.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-3ef924ee835c48d98f8dd4a0dc73ee24
出典データセット
uspto-grants-1994_05
特許番号
US05310904

関連ノート

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