Ammonia → 7-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacid

HRID 543540

반응식

HRID 543540 반응식
[NH2:1][CH:2]1[C:21](=[O:22])[N:4]2[C:5]([C:18]([OH:20])=[O:19])=[C:6]([CH2:9]OC(=O)CCC(O)=O)[CH2:7][S:8][C@H:3]12.[SH:23][C:24]1[N:28]([CH3:29])[N:27]=[N:26][N:25]=1.COC(C1C(Cl)=C(Cl)C(C(OC)=O)=C(Cl)C=1Cl)=O.N>C(#N)C>[NH2:1][CH:2]1[C:21](=[O:22])[N:4]2[C:5]([C:18]([OH:20])=[O:19])=[C:6]([CH2:9][S:23][C:24]3[N:28]([CH3:29])[N:27]=[N:26][N:25]=3)[CH2:7][S:8][C@H:3]12

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 2943DacthalHCID 70463736HCID 70463736, 화합물HCID 178482017HCID 178482017, 화합물

생성물 1

HCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacid수율 88%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A 4.0 ml portion of acetonitrile was added to 0.826 g of 7-amino-3-(3-carboxypropionyloxy)methyl-3-cephem-4-carboxylic acid and 0.32 g of 5-mercapto-1-methyl-1H-tetrazole, and 3.71 g of DCPA was added through a dropping funnel to the mixture under cooling at -5° to 0° C., followed by rinsing the funnel with 0.5 ml of acetonitrile. The mixture was stirred at the same temperature and turned into a solution. Then, the reaction solution was stirred for 45 minutes at 14° to 15° C. to allow the reaction to proceed. The reaction solution was cooled with ice, and poured into ice-water, which was placed in a refrigerator overnight and adjusted to pH 4.0 with 25% aqueous ammonia. The precipitated powder was recovered by filtration, washed with water and acetone successively, and dried, thereby affording 0.722 g (88.0% of yield) of 7-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid. The IR and NMR values of the product were in accordance with those of the authentic sample.

후처리

  1. additionwas added through a dropping funnel to the mixture
  2. temperatureunder cooling at -5° to 0° C.
  3. washby rinsing the funnel with 0.5 ml of acetonitrile
  4. stirringThen, the reaction solution was stirred for 45 minutes at 14° to 15° C.
  5. customthe reaction
  6. temperatureThe reaction solution was cooled with ice
  7. customwas placed in a refrigerator overnight
  8. filtrationThe precipitated powder was recovered by filtration
  9. washwashed with water and acetone successively
  10. customdried

출처 및 근거

ORD 기록
ord-38ad118902834c5099dd535d6bec4efd
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04446318

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