Phosphorus oxychloride → HCID 131714064, 화합물

HRID 569453

반응식

HRID 569453 반응식
P(Cl)(Cl)(Cl)=O.[N+:6]([C:9]1[CH:33]=[CH:32][C:12]([CH2:13][O:14][C:15]([CH2:17][O:18][N:19]=[C:20]([C:24]2[N:25]=[C:26]([NH:29][CH:30]=[O:31])[S:27][CH:28]=2)[C:21]([OH:23])=O)=[O:16])=[CH:11][CH:10]=1)([O-:8])=[O:7].[NH2:34][CH:35]1[C:47](=[O:48])[N:37]2[C:38]([C:44]([OH:46])=[O:45])=[C:39]([CH:42]=[CH2:43])[CH2:40][S:41][C@H:36]12.C[Si](CC(N)=O)(C)C>O1CCCC1.C(OCC)(=O)C.O.CN(C)C=O>[N+:6]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][O:14][C:15]([CH2:17][O:18][N:19]=[C:20]([C:24]2[N:25]=[C:26]([NH:29][CH:30]=[O:31])[S:27][CH:28]=2)[C:21]([NH:34][CH:35]2[C:47](=[O:48])[N:37]3[C:38]([C:44]([OH:46])=[O:45])=[C:39]([CH:42]=[CH2:43])[CH2:40][S:41][C@H:36]23)=[O:23])=[O:16])=[CH:32][CH:33]=1)([O-:8])=[O:7]

참가 물질

9

반응물 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128180067-Amino-3vinyl-3-cephem-4-carboxylic acidHCID 54535272HCID 54535272, 화합물

생성물 1

HCID 131714064HCID 131714064, 화합물수율 73.4%

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

실험 절차

Vilsmeir reagent was prepared from N,N-dimethylformamide (1.67 ml) and phosphorus oxychloride (1.98 ml) in dry tetrahydrofuran (50.4 ml) in a conventional manner. 2-(p-Nitrobenzyloxycarbonylmethoxyimino)-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (7.35 g) was added to the stirred suspension of Vilsmeir reagent under ice-cooling, followed by stirring for 30 minutes at the same temperature. To a solution of 7-amino-3-vinyl-3-cephem-4-carboxylic acid (3.4 g) and trimethylsilylacetamide (11.8 g) in ethyl acetate (35 ml) was added the activated acid solution obtained above at -20° C., and the reaction mixture was stirred at -20° C. to -10° C. for an hour. After water and ethyl acetate were added to the resultant solution, the separated organic layer was washed with water and then dried. A conventional work-up of the solution gave 7-[2-(p-nitrobenzyloxycarbonylmethoxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (6.8 g) as yellowish powder.

후처리

  1. temperaturecooling
  2. customobtained above at -20° C.
  3. stirringthe reaction mixture was stirred at -20° C. to -10° C. for an hour
  4. washthe separated organic layer was washed with water
  5. customdried

출처 및 근거

ORD 기록
ord-7578d60fee124d5783a94b5f98871e45
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04731443

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