Sodium Methoxide → 2-t-Butoxycarbonylmethoxyimino-2-(3-chloro-4-hydroxyphenyl)acetic acid

HRID 463840노트

반응식

HRID 463840 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[C:14]([O:18][C:19]([CH2:21][O:22][NH2:23])=[O:20])([CH3:17])([CH3:16])[CH3:15].C[O-].[Na+]>CO>[C:14]([O:18][C:19]([CH2:21][O:22][N:23]=[C:9]([C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([Cl:1])[CH:3]=1)[C:10]([OH:12])=[O:11])=[O:20])([CH3:17])([CH3:16])[CH3:15]

참가 물질

5

반응물 3

HCID 10942334Sodium MethoxideHCID 12919121tert-Butyl (aminooxy)acetateHCID 129611392-(3-Chloro-4-hydroxyphenyl)-2-oxoacetic acid

생성물 1

HCID 1361491122-t-Butoxycarbonylmethoxyimino-2-(3-chloro-4-hydroxyphenyl)acetic acid수율 79.1%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

A mixture of 2-(3-chloro-4-hydroxyphenyl)glyoxylic acid (2.0 g.), O-t-butoxycarbonylmethylhydroxylamine (1.62 g.) and methanol (20 ml.) was adjusted to pH 5 to 6 by adding an 1N methanol solution of sodium methoxide and stirred for 3 hours at ambient temperature. The reaction mixture was concentrated to dryness under reduced pressure and the residue was dissolved in an 1N aqueous solution of sodium hydroxide to adjust to pH 7.0. The aqueous solution was washed with ether, adjusted to pH 2.0 with 10% hydrochloric acid under ice-cooling and extracted with ether. The extract was washed with water and dried over magnesium sulfate. The solution was concentrated to dryness under reduced pressure to give crystals of 2-t-butoxycarbonylmethoxyimino-2-(3-chloro-4-hydroxyphenyl)acetic acid (syn isomer) (2.6 g.), mp 116° to 118° C. (dec.).

후처리

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in an 1N aqueous solution of sodium hydroxide
  3. washThe aqueous solution was washed with ether
  4. temperaturecooling
  5. extractionextracted with ether
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solution was concentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-2e74ef3c846a4494aac5618916fa4ebe
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04544653

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