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Hydrochloric Acid → (1R,2R,4R)-2-(tert-butoxycarbonyl)-4-(tert-butyldiphenylsilyloxy)cyclohexanecarboxylic acid

HRID 530707
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HRID 530707 반응식
C[O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@@H:8]([O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][C@H:6]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:4].[Li+].[OH-].Cl>C1COCC1.O>[C:32]([O:31][C:29]([C@@H:6]1[CH2:7][C@H:8]([O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:9][CH2:10][C@H:5]1[C:3]([OH:4])=[O:2])=[O:30])([CH3:35])([CH3:33])[CH3:34]
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58282737(1R,2R,4R)-2-tert-butyl 1-methyl 4-(tert-butyldiphenylsilyloxy)cyclohexane-1,2-dicarboxylate

생성물 1

HCID 58282618(1R,2R,4R)-2-(tert-butoxycarbonyl)-4-(tert-butyldiphenylsilyloxy)cyclohexanecarboxylic acid수율 63%

시약·촉매·용매 1

HCID 21881883
Oxolane--water (1/1)
용매

실험 절차

A solution of compound 7 (4.2 mmol) and LiOH (16.8 mmol) in THF/H2O 1/1 (40 mL) was stirred at room temperature for 16 hrs. The reaction mixture was neutralized with 1N HCl to pH 2, and then extracted with DCM (100 mL). Organics were concentrated under reduced pressure and purified by chromatography on silica gel (Cyclohexane/EtOAc) to yield compound 8 as pale yellow oil in 63% yield.

후처리

  1. extractionextracted with DCM (100 mL)
  2. concentrationOrganics were concentrated under reduced pressure
  3. custompurified by chromatography on silica gel (Cyclohexane/EtOAc)

출처 및 근거

ORD 기록
ord-37184622fae6465b8af571bd9636471e
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09353100B2

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