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Hydrochloric Acid → 4-Cyclopropylmethyl-1-(4'-fluoro-biphenyl-4-carbonyl)-piperidine-4-carboxylic acid

HRID 2189984
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HRID 2189984 반응식
C([O:3][C:4]([C:6]1([CH2:27][CH:28]2[CH2:30][CH2:29]2)[CH2:11][CH2:10][N:9]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[O:13])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[CH:28]1([CH2:27][C:6]2([C:4]([OH:5])=[O:3])[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)=[O:13])[CH2:8][CH2:7]2)[CH2:30][CH2:29]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 595279394-Cyclopropylmethyl-1-(4'-fluoro-biphenyl-4-carbonyl)-piperidine-4-carboxylic acid ethyl ester

생성물 1

HCID 595277804-Cyclopropylmethyl-1-(4'-fluoro-biphenyl-4-carbonyl)-piperidine-4-carboxylic acid

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
75 °C

실험 절차

A mixture of 0.51 g (1.24 mmol) 4-cyclopropylmethyl-1-(4′-fluoro-biphenyl-4-carbonyl)-piperidine-4-carboxylic acid ethyl ester and 1.87 mL 4N NaOH aq. in 5 mL ethanol was stirred at 75° C. for a prolonged period of time. After concentration of the mixture ice-water was added and the pH was adjusted to pH=2 with HCl aq. The mixture was extracted with ethyl acetate, the combined organic layers were dried with Na2SO4, filtered, evaporated to dryness and purified by column chromatography on silica eluting with a gradient formed from ethyl acetate, heptane and formic acid to yield after evaporation of the product containing fractions 0.146 g (31%) of the title compound as white foam. MS ISP (m/e): 382.3 [(M+H)+].

후처리

  1. extractionwas extracted with ethyl acetate
  2. dry with materialthe combined organic layers were dried with Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. custompurified by column chromatography on silica eluting with a gradient
  6. customformed from ethyl acetate, heptane and formic acid
  7. customto yield
  8. customafter evaporation of the product
  9. additioncontaining fractions 0.146 g (31%) of the title compound as white foam

출처 및 근거

ORD 기록
ord-201eb397257040f89199e4e3c2ea58f2
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08324250B2

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