Trifluoroacetic acid → 2-Tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetic acid

HRID 358081노트

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HRID 358081 반응식
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:28]1[N:32]=[CH:31][S:30][N:29]=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:32]=[CH:31][S:30][N:29]=1)[C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 8857Ethyl AcetateHCID 54175448Benzhydryl 2-tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetate

생성물 1

HCID 539872492-Tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetic acid수율 53.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of benzhydryl 2-tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetate (syn isomer) (6.5 g) and anisole (6.5 ml) in methylene chloride (60 ml) was added trifluoroacetic acid (13 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 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 an aqueous sodium chloride, and dried over magnesium sulfate. The solution was evaporated and the residue was pulverized with diisopropyl ether and n-hexane to give 2-tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetic acid (syn isomer) (2.2 g), mp. 137° C. (dec.).

후처리

  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 an aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customThe solution was evaporated

출처 및 근거

ORD 기록
ord-8a30580c085443c4b2c02380d86d5a51
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04464369

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