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

HRID 2189984
ノート
印刷プレビュー

反応式

HRID 2189984 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
75 °C

実験手順

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)+].

後処理

  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

出典と根拠

ORDレコード
ord-201eb397257040f89199e4e3c2ea58f2
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08324250B2

反応ノート

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