Hydrochloric Acid → HCID 178519972, 화합물

HRID 2169366노트

반응식

HRID 2169366 반응식
[Si]([O:8][CH2:9][CH2:10][N:11]([CH2:42][CH:43]1[CH2:45][CH2:44]1)[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:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl.C(OCC)(=O)C>O1CCCC1>[CH:43]1([CH2:42][N:11]([CH2:10][CH2:9][OH:8])[C:12]([C:14]2[C:19]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]3([C:35]4[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=4)[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:15]=2)=[O:13])[CH2:45][CH2:44]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178455249HCID 178455249, 화합물

생성물 1

HCID 178519972HCID 178519972, 화합물수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropylmethyl-amide (329) (580 mg, crude) in tetrahydrofuran (30 mL) was added 1N aq.HCl (6 mL) at room temperature and stirring was continued for 1 h (TLC; 100% ethyl acetate/UV/SiO2, Rf=0.2). Tetrahydrofuran was removed in vacuo and the crude mass was dissolved in ethyl acetate (50 mL) and washed with NaHCO3 solution (10 mL), water (20 mL) and brine (20 mL); The organic phase was dried and concentrated in vacuo to get a crude mass which was purified by CombiFlash using a gradient eluent mixture of ethyl acetate and hexane to get pure 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid cyclopropylmethyl-(2-hydroxyethyl)-amide (330) (390 mg, 94% two steps) as an off-white sticky solid.

후처리

  1. customTetrahydrofuran was removed in vacuo
  2. dissolutionthe crude mass was dissolved in ethyl acetate (50 mL)
  3. washwashed with NaHCO3 solution (10 mL), water (20 mL) and brine (20 mL)
  4. customThe organic phase was dried
  5. concentrationconcentrated in vacuo
  6. customto get a crude mass which
  7. customwas purified by CombiFlash
  8. additiona gradient eluent mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-cf9718e89474471bb2f393af4d4fb578
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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