Water → HCID 70462314, 화합물

HRID 543543

반응식

HRID 543543 반응식
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.O.[SH:20][C:21]1[S:25][C:24]([S:26][CH2:27][C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[O:29])=[N:23][N:22]=1.P(Cl)(Cl)(OP(Cl)(Cl)=O)=O>C(#N)C>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:20][C:21]3[S:25][C:24]([S:26][CH2:27][C:28]([N:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)=[O:29])=[N:23][N:22]=3)[CH2:15][S:14][C@H:9]12

참가 물질

6

반응물 4

HCID 962WaterHCID 4413287-Aminocephalosporanic acidHCID 4432411Diphosphoryl tetrachlorideHCID 178521532HCID 178521532, 화합물

생성물 1

HCID 70462314HCID 70462314, 화합물수율 90%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

Mixed were 0.68 g of 7-ACA, 0.18 g of water and 0.90 g of 5-mercapto-2-morpholinocarbonylmethylthio-1,3,4-thiadiazole, and 4.0 ml of acetonitrile was added to the mixture, 2.52 g of diphosphoryl tetrachloride was added to the mixture under stirring in a dry ice/acetone bath at -20° to -40° C. over a period of about 10 minutes, and the cooling bath was removed. After the temperature was allowed to increase at 0° C., the reaction solution was stirred in a warm water bath at 40° C. for 20 minutes, cooled with ice and adjusted to pH 4.3 with aqueous concentrated ammonia following the addition of 5 ml of water. There was obtained 1.10 g (89.9% of yield) of 7-amino-3-(2-morpholinocarbonylmethylthio-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid thus produced.

후처리

  1. additionMixed
  2. additionwas added to the mixture
  3. customthe cooling bath was removed
  4. stirringthe reaction solution was stirred in a warm water bath at 40° C. for 20 minutes
  5. temperaturecooled with ice
  6. additionthe addition of 5 ml of water

출처 및 근거

ORD 기록
ord-fdc14065cefd49e48de1c3f236715201
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04446318

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