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

HRID 1065879ノート

反応式

HRID 1065879 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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 1 N 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 1 N 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.).

後処理

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in an 1 N 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

出典と根拠

ORDレコード
ord-090107a2714243b794b78b88c965f10b
出典データセット
uspto-grants-1982_05
特許番号
US04331664

反応ノート

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