Sulfuric Acid → 2-n-Octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-cephem-4-carboxylate

HRID 1632752노트

반응식

HRID 1632752 반응식
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH3:27])[C:10]([NH:12][CH:13]2[C:23](=[O:24])[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].[CH2:28]([O:36][CH2:37][CH:38]([CH2:40][O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])O)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].C1(S(Cl)(=O)=O)C=CC=CC=1.S(=O)(=O)(O)O>N1C=CC=CC=1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH3:27])[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[CH:16]([C:20]([O:22][CH:38]([CH2:37][O:36][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:40][O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[O:21])[CH:17]=[CH:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 7369Benzenesulfonyl chlorideHCID 40492571,3-Dioctyl glyceryl etherHCID 1317124427-[2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

생성물 1

HCID 1317139162-n-Octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-cephem-4-carboxylate수율 30%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 6.0 g) and molecular sieves (20 g) in dry pyridine (60 ml) was stirred at 0° to 5° C. for an hour, and 2-n-octyloxy-1-n-octyloxymethylethanol [4.6 g] was added thereto. Benzenesulfonyl chloride (2.6 g) was dropwise added to the stirred solution at -5° to -3° C. over 30 minutes, and then stirred at 0° C. for an hour. The resultant mixture was poured into the crushed ice (300 g), adjusted to pH 1 to 2 with 20% sulfuric acid, and then extracted with ethyl acetate (300 ml). The extract was washed with a saturated aqueous solution of sodium chloride, an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, and dried over anhydrous magnesium sulfate. The solution was evaporated under reduced pressure, and the residue was subjected to column chromatography on silica gel (200 g) with a mixture of chloroform and methanol (20:1). The eluate was evaporated in vacuo to give powder [3.1 g] of 2-n-octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-cephem-4-carboxylate (syn isomer).

후처리

  1. stirringstirred at 0° C. for an hour
  2. extractionextracted with ethyl acetate (300 ml)
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialan aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, and dried over anhydrous magnesium sulfate
  5. customThe solution was evaporated under reduced pressure
  6. additionthe residue was subjected to column chromatography on silica gel (200 g) with a mixture of chloroform and methanol (20:1)
  7. customThe eluate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-0017c205d8ed4825b31a0652dd58c8da
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04477447

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