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

HRID 543539

反応式

HRID 543539 の反応式
[NH2:1][CH:2]1[C:25](=[O:26])[N:4]2[C:5]([C:22]([OH:24])=[O:23])=[C:6]([CH2:9]OC(=O)C3C=CC=CC=3C(O)=O)[CH2:7][S:8][C@H:3]12.[SH:27][C:28]1[N:32]([CH3:33])[N:31]=[N:30][N:29]=1.COC(C1C(Cl)=C(Cl)C(C(OC)=O)=C(Cl)C=1Cl)=O>C(#N)C>[NH2:1][CH:2]1[C:25](=[O:26])[N:4]2[C:5]([C:22]([OH:24])=[O:23])=[C:6]([CH2:9][S:27][C:28]3[N:32]([CH3:33])[N:31]=[N:30][N:29]=3)[CH2:7][S:8][C@H:3]12

参加物

5

反応物 3

HCID 2943DacthalHCID 70463326HCID 70463326、化合物HCID 178482017HCID 178482017、化合物

生成物 1

HCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacid収率 86.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

A 3.5 ml portion of acetonitrile was added to 0.946 g of 7-amino-3-(2-carboxybenzoyloxy)methyl-3-cephem-4-carboxylic acid and 0.32 g of 5-mercapto-1-methyl-1H-tetrazole, and the mixture was cooled over a dry-ice/ethanol bath, followed by adding through a dropping funnel 3.71 g of DCPA to it with stirring and rinsing the funnel with 1.0 ml of acetonitrile. The external bath was removed, and the reaction mixture was warmed to 0° C., whereby the starting materials dissolved. The solution was stirred at 14° to 16° C. for 40 minutes to allow the reaction to proceed, and the reaction solution was cooled with ice, and poured into ice-water, which was placed in a refrigerator overnight. The precipitate was filtered out and washed with 10 ml of water, and the filtrate and washing were combined and adjusted to pH 4.0 with 25% aqueous ammonia under ice cooling. The precipitated powder was recovered by filtration, washed with water and acetone successively, and dried, thereby affording 0.710 g (86.5% 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.

後処理

  1. temperaturethe mixture was cooled over a dry-ice/ethanol bath
  2. washrinsing the funnel with 1.0 ml of acetonitrile
  3. customThe external bath was removed
  4. dissolutionwhereby the starting materials dissolved
  5. stirringThe solution was stirred at 14° to 16° C. for 40 minutes
  6. customthe reaction
  7. temperaturethe reaction solution was cooled with ice
  8. customwas placed in a refrigerator overnight
  9. filtrationThe precipitate was filtered out
  10. washwashed with 10 ml of water
  11. washthe filtrate and washing
  12. filtrationThe precipitated powder was recovered by filtration
  13. washwashed with water and acetone successively
  14. customdried

出典と根拠

ORDレコード
ord-85c49044718c4f0c915c14e5dbcdb505
出典データセット
uspto-grants-1984_05
特許番号
US04446318

関連ノート

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