Ethanol → 7-[[(2-amino-4-thiazolyl)-2-oxoacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-carboxylic acid

HRID 375267Notes

Reaction equation

HRID 375267 reaction equation
[NH2:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][S:10][C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12.S1C2C=CC=CC=2N=C1S[C:32](=[O:41])[C:33]([C:35]1[N:36]=[C:37]([NH2:40])[S:38][CH:39]=1)=[O:34].C(O)C>ClCCl>[NH2:40][C:37]1[S:38][CH:39]=[C:35]([C:33](=[O:34])[C:32]([NH:1][CH:2]2[C:20](=[O:21])[N:4]3[CH:3]2[S:8][CH2:7][C:6]([CH2:9][S:10][C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)=[C:5]3[C:17]([OH:19])=[O:18])=[O:41])[N:36]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacidHCID 137285792-Amino-alpha-oxo-4-thiazoleethanethioic Acid S-2-Benzothiazolyl Ester

Product 1

HCID 137285807-[[(2-amino-4-thiazolyl)-2-oxoacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.29 g of 7-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]ceph-3-em-4-carboxylic acid are suspended in 25 ml of dichloromethane and mixed with 2.7 ml of N,O-bis-(trimethylsilyl)acetamide. After 15 minutes, a clear solution is present. This is cooled to -15°, and 3.9 g of 2-(2-aminothiazol-4-yl)-2-oxothioacetic-acid-S-benzothiazol-2-ylester are added. After stirring for four hours at -15°, the preparation is stirred into 100 ml of ethanol, whereby the end product precipitates. This is stirred for one hour at 0°, filtered, washed with ethanol and vacuum dried. Yield: 3.9 g, i.e. 80.7%. M.p.: from 145° (decomp.).

Workup

  1. temperatureThis is cooled to -15°
  2. customprecipitates
  3. stirringThis is stirred for one hour at 0°
  4. filtrationfiltered
  5. washwashed with ethanol and vacuum
  6. customdried

Sources & evidence

ORD record
ord-ac9b1b7057944ef5800fea2b345bfdd4
Source dataset
uspto-grants-1996_01
Patent number
US05484928

Reaction notes

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