Hydrochloric Acid → 2-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid

HRID 648833노트

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HRID 648833 반응식
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:15]1[N:16]=[C:17](N)[S:18][CH:19]=1)[C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].N(OC(C)(C)C)=O.Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:15]1[N:16]=[CH:17][S:18][CH:19]=1)[C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 11430Potassium CarbonateHCID 53395219HCID 53395219, 화합물

생성물 1

HCID 544727372-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid수율 55.8%

시약·촉매·용매 3

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 2-t-butoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetic acid (syn isomer) (11.5 g) in tetrahydrofuran (80.5 ml) was added dropwise a solution of t-butyl nitrite (6.5 g) in tetrahydrofuran (32.5 ml) at 50 to 57° C. under stirring, and the mixture was stirred at 50 to 55° C. for 20 minutes. The reaction mixture was poured into a mixture of ethyl acetate and water and the solution was acidified to pH 1.0 with 10% hydrochloric acid. Water (60 ml) was added to the separated organic layer and the mixture was adjusted to pH 6.0 with 40% aqueous solution of potassium carbonate. The separated aqueous solution was washed with ethyl acetate and the solution was acidified to pH 2.8 with 10% hydrochloric acid. The acidified solution was extracted with ethyl acetate and the ethyl acetate layer was dried over magnesium sulfate and evaporated. The residue was triturated with diisopropyl ether to give 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid (syn isomer) (6.1 g), mp. 141° C. (dec.).

후처리

  1. stirringthe mixture was stirred at 50 to 55° C. for 20 minutes
  2. washThe separated aqueous solution was washed with ethyl acetate
  3. extractionThe acidified solution was extracted with ethyl acetate
  4. dry with materialthe ethyl acetate layer was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was triturated with diisopropyl ether

출처 및 근거

ORD 기록
ord-b5e517384c6f408194e4d0152e54392b
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04736039

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