Potassium Hydroxide → HCID 54161940, 화합물

HRID 5841노트

반응식

HRID 5841 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[S:13][C:12]3[CH:14]=[CH:15][C:16]4[C:21]([C:11]=3[N:10](C(=O)[C@@H]3CCCN3S(C3C=CC5C(=CC=CC=5)C=3)(=O)=O)[CH2:9]2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[S:13][C:12]3[CH:14]=[CH:15][C:16]4[C:21]([C:11]=3[NH:10][CH2:9]2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 54292589(R)-3-(4-chlorophenyl)-1-[(S)-N-(2-naphthalenesulfonyl)prolyl]-2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine

생성물 1

HCID 54161940HCID 54161940, 화합물수율 63.1%

시약·촉매·용매 1

HCID 19096565Water ethanol용매

실험 절차

A mixture of (R)-3-(4-chlorophenyl)-1-[(S)-N-(2-naphthalenesulfonyl)prolyl]-2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine (11.50 g, 0.019 mole), 86 % potassium hydroxide (15.0 g, 0.227 mole) and ethanol-water (10:1, 230 ml) is refluxed under argon for one hour. The reaction mixture is poured into ice water and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed with water and saline, dried over sodium sulfate and distilled to remove the solvent. The residue is purified by silica gel column chromatography (CHCl3) and thereafter recrystallized from ethyl acetate-hexane to give (R)-(+)-3-(4-chlorophenyl)- 2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine (3.74 g, 63%). M.p. 205°-206° C.

후처리

  1. temperatureis refluxed under argon for one hour
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe ethyl acetate layer is washed with water and saline
  4. dry with materialdried over sodium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (CHCl3)
  8. customrecrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-b83e9eb589e24776b7e8c40b1d8b288f
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246929

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