Trifluoroacetic acid → 2-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid

HRID 462595ノート

反応式

HRID 462595 の反応式
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:28]1[N:29]=[CH:30][S:31][CH:32]=1)[C:12]([O:14]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OCC)(=O)C>C(Cl)Cl>[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:28]1[N:29]=[CH:30][S:31][CH:32]=1)[C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 8857Ethyl AcetateHCID 54223791Benzhydryl 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetate

生成物 1

HCID 544727372-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid収率 76.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of benzhydryl 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetate (syn isomer) (2.2 g) and anisole (2.2 ml) in methylene chloride (22 ml) was added trifluoroacetic acid (4 ml) at ambient temperature and the mixture was stirred at the same temperature for 25 minutes. To the reaction mixture was added ethyl acetate and the solution was washed with water. To the separated organic layer was added water and the mixture was adjusted to pH 7.5 with 20% aqueous solution of sodium carbonate. The separated aqueous layer was acidified to pH 2.0 with 10% hydrochloric acid. The acidified solution was saturated with sodium chloride and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, and dried over magnesium sulfate. The solution was evaporated and the residue was pulverized with diisopropyl ether and n-hexane to give 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid (syn isomer) (1.07 g), mp. 136°-139° C.

後処理

  1. washthe solution was washed with water
  2. additionTo the separated organic layer was added water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solution was evaporated

出典と根拠

ORDレコード
ord-ec5ccebb971d4594a6099c30794ede2b
出典データセット
uspto-grants-1985_05
特許番号
US04515788

反応ノート

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