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

HRID 375269Notes

Reaction equation

HRID 375269 reaction equation
[NH2:1][CH:2]1[C:13](=[O:14])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[C:6]([CH3:9])[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:37](=[O:46])[C:38]([C:40]1[N:41]=[C:42]([NH2:45])[S:43][CH:44]=1)=[O:39]>ClCCl>[NH2:45][C:42]1[S:43][CH:44]=[C:40]([C:38](=[O:39])[C:37]([NH:1][CH:2]2[C:13](=[O:14])[N:4]3[C:5]([C:10]([OH:12])=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]23)=[O:46])[N:41]=1

Participants

5

Reactant 3

HCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 13475828(6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 137285792-Amino-alpha-oxo-4-thiazoleethanethioic Acid S-2-Benzothiazolyl Ester

Product 1

HCID 883932567-[[(2-Amino-4-thiazolyl)-2-oxoacetyl]amino]-3-methylceph-3-em-4-carboxylic acidYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.28 g of 7-amino-3-methylceph-3-em-4-carboxylic acid are suspended under a nitrogen atmosphere in 80 ml of dry dichloromethane, 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 one hour at -15°, one hour at 0° and then two hours at +20°. The solvent is carefully drawn off on a rotary evaporator, and the oily residue is rubbed with 50 ml of ethanol. The resultant deposit is filtered, washed with ethanol and ether, and vacuum dried at 40°. 5.3 g of the title compound are obtained as a yellow powder.

Workup

  1. temperaturecooled to -15°
  2. stirringstirred for one hour at -15°, one hour at 0°
  3. customtwo hours
  4. customat +20°
  5. customThe solvent is carefully drawn off on a rotary evaporator
  6. filtrationThe resultant deposit is filtered
  7. washwashed with ethanol and ether, and vacuum
  8. customdried at 40°

Sources & evidence

ORD record
ord-2bdc9bbfa8c24f89809d616564fca398
Source dataset
uspto-grants-1996_01
Patent number
US05484928

Reaction notes

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