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4-Nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate → 7-[2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 364512
ノート
印刷プレビュー

反応式

HRID 364512 の反応式
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:35][O:36][CH3:37])[C:10]([NH:12][CH:13]2[C:33](=[O:34])[N:15]3[C:16]([C:20]([O:22]CC4C=CC([N+]([O-])=O)=CC=4)=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]>CO.O1CCCC1.[C].[Pd]>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:35][O:36][CH3:37])[C:10]([NH:12][CH:13]2[C:33](=[O:34])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

HCID 1317124414-Nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

生成物 1

HCID 1317124427-[2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid収率 63.8%

試薬・触媒・溶媒 3

HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran
溶媒

実験手順

To a solution of p-nitrobenzyl 7-{2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido}-3-cephem-4-carboxylate (syn isomer, 1.25 g.) in methanol (40 ml.) and tetrahydrofuran (50 ml.) was added 10% palladium carbon (0.65 g.), and the mixture was subjected to catalytic reduction at room temperature under atmospheric pressure for 3.5 hours. After removing the catalyst from the reaction mixture, the filtrate was concentrated under reduced pressure. Water (80 ml.) was added to the residue, and the mixture was adjusted to pH 7.5 with an aqueous solution of sodium bicarbonate, and then the insoluble substance was filtered off. The filtrate was washed with ethyl acetate (50 ml.), and then ethyl acetate (100 ml.) was added to the solution. After adjusting to pH 1.5 with 10% hydrochloric acid, the ethyl acetate layer was separated. The remaining aqueous layer was extracted with ethyl acetate (80 ml.) twice, and the extracts were combined with the ethyl acetate layer obtained above, washed with an aqueous solution of sodium chloride, dried over magnesium sulfate, and then concentrated under reduced pressure to give 7-{2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido}-3-cephem-4-carboxylic acid (syn isomer, 0.60 g.), m.p. 176° to 183° C. (dec.).

後処理

  1. customAfter removing the catalyst from the reaction mixture
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater (80 ml.) was added to the residue
  4. filtrationthe insoluble substance was filtered off
  5. washThe filtrate was washed with ethyl acetate (50 ml.)
  6. additionethyl acetate (100 ml.) was added to the solution
  7. customthe ethyl acetate layer was separated
  8. extractionThe remaining aqueous layer was extracted with ethyl acetate (80 ml.) twice
  9. customobtained above,
  10. washwashed with an aqueous solution of sodium chloride
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d59a6618e6574c56bf32ac73220a8c95
出典データセット
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04604456

反応ノート

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