N,O-bis(trimethylsilyl)acetamide → 7-[[(2-Amino-4-thiazolyl)-2-oxoacetyl]amino]-3-acetoxymethylceph-3-em-4-carboxylic acid

HRID 375268Notes

Reaction equation

HRID 375268 reaction equation
[NH2:1][CH:2]1[C:17](=[O:18])[N:4]2[C:5]([C:14]([OH:16])=[O:15])=[C:6]([CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH2:7][S:8][C@H:3]12.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.S1C2C=CC=CC=2N=C1S[C:41](=[O:50])[C:42]([C:44]1[N:45]=[C:46]([NH2:49])[S:47][CH:48]=1)=[O:43]>ClCCl>[NH2:49][C:46]1[S:47][CH:48]=[C:44]([C:42](=[O:43])[C:41]([NH:1][CH:2]2[C:17](=[O:18])[N:4]3[C:5]([C:14]([OH:16])=[O:15])=[C:6]([CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH2:7][S:8][C@H:3]23)=[O:50])[N:45]=1

Participants

5

Reactant 3

HCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 113463103-Acetoxymethyl-7-amino-3cephem-4-carboxylic acidHCID 137285792-Amino-alpha-oxo-4-thiazoleethanethioic Acid S-2-Benzothiazolyl Ester

Product 1

HCID 705316737-[[(2-Amino-4-thiazolyl)-2-oxoacetyl]amino]-3-acetoxymethylceph-3-em-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.44 g of 7-amino-3-acetoxymethylceph-3-em-4-carboxylic acid are suspended under a nitrogen atmosphere in 50 ml of dry di-chloromethane, and mixed with 5.4 ml of N,O-bis(trimethylsilyl)acetamide. The preparation is stirred at room temperature until a clear solution is present, and then cooled to -15°. 8.4 g of 2-(2-amino-4-thiazolyl)-2-oxothioacetic-acid-S-benzothiazol-2-ylester are added, and stirred for two hours at -15° and then for two hours at 0°. The solvent is carefully drawn off in a rotary evaporator, and the oily residue is rubbed with 50 ml of ethanol, whereby the title compound precipitates. 6.3 g are obtained in the form of a yellow powder.

Workup

  1. temperaturecooled to -15°
  2. stirringstirred for two hours at -15°
  3. customThe solvent is carefully drawn off in a rotary evaporator
  4. customprecipitates
  5. custom6.3 g are obtained in the form of a yellow powder

Sources & evidence

ORD record
ord-1e373d5ca7764b0b9fb8150418000105
Source dataset
uspto-grants-1996_01
Patent number
US05484928

Reaction notes

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