Hydrochloric Acid → HCID 178457437, 화합물

HRID 2169295노트

반응식

HRID 2169295 반응식
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:42]([CH3:44])[CH3:43])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]([CH:42]([CH3:44])[CH3:43])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 178457474HCID 178457474, 화합물

생성물 1

HCID 178457437HCID 178457437, 화합물수율 75.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (257) (0.7 g, 1.13 mmol) in tetrahydrofuran (10.0 mL) was added HCl (0.062 g, 1.70 mmol) and the reaction mixture was stirred at room temperature for 1.5 h. After completion of the reaction, the mixture was extracted with ethyl acetate. The combined organic layer was washed with water, separated and dried over Na2SO4. After evaporation of the solvent, the crude product was purified by normal silica gel column chromatography (using 60% ethyl acetate in hexane followed by 5% methanol in ethyl acetate) to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (258) (0.43 g, 75.0%) as a white solid.

후처리

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with water
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation of the solvent
  7. customthe crude product was purified by normal silica gel column chromatography (using 60% ethyl acetate in hexane followed by 5% methanol in ethyl acetate)

출처 및 근거

ORD 기록
ord-c09dd0da38c04b5f831538f7a2d99d62
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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