Hydrochloric Acid → 2-Benzyloxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid

HRID 1195521노트

반응식

HRID 1195521 반응식
O.NN.Cl.[NH2:5][O:6][CH2:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[CH:18]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=O)[C:27]([OH:29])=[O:28])[N:25]=1)=[O:19].[OH-].[Na+]>CO.O1CCCC1.N1C=CC=CC=1>[CH2:11]([O:10][C:8]([CH2:7][O:6][N:5]=[C:26]([C:24]1[N:25]=[C:21]([NH:20][CH:18]=[O:19])[S:22][CH:23]=1)[C:27]([OH:29])=[O:28])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 11309879Benzyl 2-(aminooxy)acetateHCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acid

생성물 1

HCID 542157752-Benzyloxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid

시약·촉매·용매 3

HCID 887Methanol용매HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of hydrazine hydrate (8.0 g) in methanol (16 ml) was added to a suspension of benzyl 2-phthalimidoxyacetate (46.0 g) in tetrahydrofuran (150 ml), and the mixture was stirred at ambient temperature for 30 minutes. To the reaction mixture was added 20% hydrochloric acid under ice-cooling, followed by stirring at the same temperature for 10 minutes. The insoluble substance was filtered off to give a solution containing benzyl 2-aminooxyacetate. To this solution were added (2-formamidothiazol-4-yl)glyoxylic acid (24.7 g) and pyridine (24.8 ml), and the mixture was stirred at ambient temperature for 3 hours. The reaction mixture was adjusted to pH 7.5 with 10% aqueous sodium hydroxide and then washed with ethyl acetate. The resultant aqueous solution was acidified to pH 2.0 with 10% hydrochloric acid, followed by extraction with ethyl acetate. The extract was washed with an aqueous sodium chloride ad then dried over magnesium sulfate. The solution was evaporated and the residue was pulverized with diisopropyl ether to give 2-benzyloxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) 37 g), mp 152° C. (dec.).

후처리

  1. temperaturecooling
  2. stirringby stirring at the same temperature for 10 minutes
  3. filtrationThe insoluble substance was filtered off
  4. customto give a solution
  5. stirringthe mixture was stirred at ambient temperature for 3 hours
  6. washwashed with ethyl acetate
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe extract was washed with an aqueous sodium chloride ad
  9. dry with materialthen dried over magnesium sulfate
  10. customThe solution was evaporated

출처 및 근거

ORD 기록
ord-3c0bbe2db37346df8c5a402c1c377e63
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05110921

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