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Methanol → 7-[2-(2-Formamidothiazol-4-yl)-2-n-propoxyiminoacetamido)-3-chloro-3-cephem-4-carboxylic acid

HRID 435332
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HRID 435332 반응식
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:36][O:37][CH2:38][CH2:39][CH3:40])[C:10]([NH:12][CH:13]2[C:34](=[O:35])[N:15]3[C:16]([C:21]([O:23]CC4C=CC([N+]([O-])=O)=CC=4)=[O:22])=[C:17]([Cl:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2].CO.O>[C].[Pd].O1CCCC1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:36][O:37][CH2:38][CH2:39][CH3:40])[C:10]([NH:12][CH:13]2[C:34](=[O:35])[N:15]3[C:16]([C:21]([OH:23])=[O:22])=[C:17]([Cl:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]
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참가 물질

6

반응물 3

HCID 887MethanolHCID 962WaterHCID 1317124674-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate

생성물 1

HCID 1317124687-[2-(2-Formamidothiazol-4-yl)-2-n-propoxyiminoacetamido)-3-chloro-3-cephem-4-carboxylic acid수율 85.7%

시약·촉매·용매 2

HCID 178418390
HCID 178418390, 화합물
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

A suspension of 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 2.4 g.), 10% palladium carbon (1.0 g.), methanol (24 ml.), water (3.6 ml.) and tetrahydrofuran (48 ml.) was subjected to catalytic reduction under ordinary pressure at room temperature. After removing insoluble substance by filtration, the filtrate was concentrated in vacuo. Water and ethyl acetate were added to the residue, and adjusted to pH 8 with a saturated aqueous solution of sodium bicarbonate. The insoluble substance was removed by filtration, and the aqueous layer was separated. Ethyl acetate was added to the solution, adjusted to pH 2.0 with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solution and extract were combined together, washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solution was concentrated in vacuo, and the residue was triturated with diethyl ether and collected by filtration to give 7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.6 g.).

후처리

  1. customwas subjected to catalytic reduction under ordinary pressure at room temperature
  2. customAfter removing insoluble substance
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionWater and ethyl acetate were added to the residue
  6. customThe insoluble substance was removed by filtration
  7. customthe aqueous layer was separated
  8. additionEthyl acetate was added to the solution
  9. extractionextracted with ethyl acetate
  10. extractionThe ethyl acetate solution and extract
  11. washwashed with a saturated aqueous solution of sodium chloride
  12. dry with materialdried over magnesium sulfate
  13. concentrationThe solution was concentrated in vacuo
  14. customthe residue was triturated with diethyl ether
  15. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-d7ed943a8b784c199c2570a46b9feb43
출처 데이터셋
uspto-grants-1983_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04400379

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