Ethyl Acetate → (R)-2-(4-Chlorophenyl)-4-[(S)-N-(2-naphthalene-sulfonyl)prolyl]-3,4-dihydro-2H-1,4-benzothiazine

HRID 5838노트

반응식

HRID 5838 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[S:9]2)=[CH:4][CH:3]=1.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[S:28]([N:31]1[CH2:38][CH2:37][CH2:36][C@H:32]1[C:33](Cl)=[O:34])(=[O:30])=[O:29].C(OCC)(=O)C>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:13][N:12]([C:33](=[O:34])[C@@H:32]3[CH2:36][CH2:37][CH2:38][N:31]3[S:28]([C:19]3[CH:20]=[CH:21][C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:18]=3)(=[O:30])=[O:29])[C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[S:9]2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 130715242-(4-chlorophenyl)-3,4-dihydro2H-1,4-benzothiazineHCID 13576782(S)-N-(2-naphthalenesulfonyl)prolyl chloride

생성물 1

HCID 54249707(R)-2-(4-Chlorophenyl)-4-[(S)-N-(2-naphthalene-sulfonyl)prolyl]-3,4-dihydro-2H-1,4-benzothiazine수율 51.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of (±)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine (10.01 g, 0.038 mole) in pyridine (150 ml) is added (S)-N-(2-naphthalenesulfonyl)prolyl chloride (18.57 g, 0.057 mole), and the mixture is stirred at room temperature for 4 hours. To the reaction mixture is added ethyl acetate, and the mixture is washed with 5 % hydrochloric acid, water, aqueous sodium hydrogen carbonate solution, water and saline in this order, and the ethyl acetate layer is separated, dried over sodium sulfate and distilled to remove the solvent. The resulting caramel is subjected to silica gel column chromatography (hexane:ethyl acetate=5:1 - 3:1). From the fraction eluted first there is obtained (R)-2-(4-chlorophenyl)-4-[(S)-N-(2-naphthalenesulfonyl)prolyl]-3,4-dihydro-2H-1,4-benzothiazine (10.75 g, 51 %) as crystals. M.p. 147°-151° C.

후처리

  1. washthe mixture is washed with 5 % hydrochloric acid, water, aqueous sodium hydrogen carbonate solution, water and saline in this order
  2. customthe ethyl acetate layer is separated
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. washFrom the fraction eluted first there

출처 및 근거

ORD 기록
ord-3eb7ef4cd26f4320b6742ccfe2056cf7
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246929

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