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

HRID 1033477

반응식

HRID 1033477 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-10 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3ef924ee835c48d98f8dd4a0dc73ee24
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05310904

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