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Sodium Hydroxide → (6-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-5-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl)acetic acid

HRID 2383313
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HRID 2383313 반응식
C([O:5][C:6](=[O:43])[CH2:7][CH:8]1[C:17]2[C:12](=[C:13]([CH3:35])[C:14]([C:18]3[N:22]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH:30]([CH3:32])[CH3:31])=[C:25]([C:33]#[N:34])[CH:24]=4)[O:20][N:19]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])CCC.[OH-].[Na+]>C(O)C>[C:33]([C:25]1[CH:24]=[C:23]([C:21]2[O:20][N:19]=[C:18]([C:14]3[C:13]([CH3:35])=[C:12]4[C:17](=[CH:16][CH:15]=3)[CH:8]([CH2:7][C:6]([OH:43])=[O:5])[N:9]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:10][CH2:11]4)[N:22]=2)[CH:28]=[CH:27][C:26]=1[O:29][CH:30]([CH3:31])[CH3:32])#[N:34]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 595910961,1-Dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

생성물 1

HCID 59591092(6-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-5-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl)acetic acid수율 101.9%

시약·촉매·용매 1

HCID 702
Ethanol
용매

실험 절차

To a solution of 1,1-dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1h)-isoquinolinecarboxylate (Preparation 21; 41 mg, 0.070 mmol) in ethanol (2 ml) was added 2N aqueous sodium hydroxide (0.070 ml, 0.139 mmol) and the resulting mixture was stirred at room temperature for ca. 3.5 h. Most of the solvent was removed and the residue was partitioned between ether and water (with dropwise addition of 2N sodium hydroxide to keep the mixture basic). The layers were separated, and the aqueous layer acidified 2N aqueous hydrochloric acid giving a white precipitate which was extracted twice with ethyl acetate. The combined ethyl acetate fractions were dried over MgSO4 and concentrated in vacuo to give the title compound (38 mg).

후처리

  1. customMost of the solvent was removed
  2. customthe residue was partitioned between ether and water (
  3. additionwith dropwise addition of 2N sodium hydroxide
  4. customThe layers were separated
  5. extractionwas extracted twice with ethyl acetate
  6. dry with materialThe combined ethyl acetate fractions were dried over MgSO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-790637ce38684c7bb734604e91dde6d6
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263620B2

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