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

HRID 648835노트

반응식

HRID 648835 반응식
[S:1]1[CH:5]=[C:4]([C:6](=O)[C:7]([OH:9])=[O:8])[N:3]=[CH:2]1.[NH2:11][O:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)(O)[O-].[Na+].Cl.[Cl-].[Na+]>CO.O.C(OCC)(=O)C>[C:17]([O:16][C:14]([CH2:13][O:12][N:11]=[C:6]([C:4]1[N:3]=[CH:2][S:1][CH:5]=1)[C:7]([OH:9])=[O:8])=[O:15])([CH3:20])([CH3:19])[CH3:18]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 12919121tert-Butyl (aminooxy)acetateHCID 13187915HCID 13187915, 화합물

생성물 1

HCID 544727372-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid수율 66.8%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-(4-thiazolyl)glyoxylic acid (2.3 g) in methanol (23 ml) and t-butyl 2-aminooxyacetate (2.6 g) was stirred for an hour at ambient temperature. The reaction mixture was added to a mixture of ethyl acetate and water and adjusted to pH 7.5 with saturated aqueous solution of sodium bicarbonate. The separated aqueous layer was adjusted to pH 2.0 with 10% hydrochloric acid and the mixture was saturated sodium chloride. The acidic mixture was extracted with ethyl acetate. The extract layer was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid (syn isomer) (2.8 g), mp. 136°-139° C.

후처리

  1. extractionThe acidic mixture was extracted with ethyl acetate
  2. washThe extract layer was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

출처 및 근거

ORD 기록
ord-217fe107818444d2a981050eb046e194
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04736039

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