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Hydrochloric Acid → 7-[3-(4-carboxy-phenyl)-1-pentyl-prop-2-ynyl]-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 2415215
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HRID 2415215 반응식
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:19]#[C:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([O:29]C)=[O:28])=[CH:23][CH:22]=3)[CH:16]=2)[C:11]([CH3:37])([CH3:36])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>C1COCC1.CO.O>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:19]#[C:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=3)[CH:16]=2)[C:11]([CH3:36])([CH3:37])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 692158867-[3-(4-methoxycarbonyl-phenyl)-1-pentyl-prop-2-ynyl]-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

생성물 1

HCID 692139537-[3-(4-carboxy-phenyl)-1-pentyl-prop-2-ynyl]-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester수율 87.5%

시약·촉매·용매 2

HCID 962
Water
용매
2회
HCID 21899815MeOH tetrahydrofuran용매

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온도
40 °C

실험 절차

A solution of 7-[3-(4-methoxycarbonyl-phenyl)-1-pentyl-prop-2-ynyl]-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (0.035 g, 0.07 mmole) in 5 mL of a 4:1 THF/methanol mixture was treated with a solution of 0.1 g of lithium hydroxide monohydrate in 2 mL of water and stirred at 40° C. for 2 hours. The mixture was diluted with 5 mL of water and the pH adjusted to 2 with 2N HCl solution. The mixture was extracted with three 10 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give 0.03 g of 7-[3-(4-carboxy-phenyl)-1-pentyl-prop-2-ynyl]-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as a yellow oil

후처리

  1. extractionThe mixture was extracted with three 10 mL portions of ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-97602948e6244fb1a67f646b8c05a903
출처 데이터셋
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06818652B2

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