Ethanol → HCID 178481958, compound

HRID 375270Notes

Reaction equation

HRID 375270 reaction equation
C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[NH2:13][CH:14]1[C:35](=[O:36])[N:16]2[C:17]([C:32]([OH:34])=[O:33])=[C:18]([CH2:21][S:22][C:23]3[N:24]([CH3:31])[N:25]=[C:26]([OH:30])[C:27](=[O:29])[N:28]=3)[CH2:19][S:20][C@H:15]12.S1C2C=CC=CC=2N=C1S[C:47](=[O:56])[C:48]([C:50]1[N:51]=[C:52]([NH2:55])[S:53][CH:54]=1)=[O:49].C(O)C>ClCCl>[NH2:55][C:52]1[S:53][CH:54]=[C:50]([C:48](=[O:49])[C:47]([NH:13][CH:14]2[C:35](=[O:36])[N:16]3[C:17]([C:32]([OH:34])=[O:33])=[C:18]([CH2:21][S:22][C:23]4[N:24]([CH3:31])[N:25]=[C:26]([OH:30])[C:27](=[O:29])[N:28]=4)[CH2:19][S:20][C@H:15]23)=[O:56])[N:51]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 137285792-Amino-alpha-oxo-4-thiazoleethanethioic Acid S-2-Benzothiazolyl EsterHCID 178481957HCID 178481957, compound

Product 1

HCID 178481958HCID 178481958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

14.85 ml of N,O-bis(trimethylsilyl)acetamide are added at 30° to 7.4 g of 7-amino-3-[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazin-3-yl)thiomethyl]ceph-3-em-4-carboxylic acid (water content: 3.7%) in 50 ml of dichloromethane. After two hours at 30°, the mixture is cooled to -15°. 8.1 g of 2-(2-amino-4-thiazolyl)-2-oxothioacetic-acid-S-benzothiazol-2-ylester are added, and stirred for six hours at -15°. The preparation is added to 500 ml of ethanol which has been warmed to 50°, then cooled whilst stirring and stirred for one hour at 0°. The deposit is filtered off, washed and dried. 9.1 g of the title compound are obtained as a yellow powder. IR: 3320 NH, 1805 c=o, 1735 c=o, 1690 c=o, 1645 (amide I), 1555 (amide II).

Workup

  1. temperaturethe mixture is cooled to -15°
  2. temperaturehas been warmed to 50°
  3. temperaturecooled
  4. stirringwhilst stirring
  5. stirringstirred for one hour at 0°
  6. filtrationThe deposit is filtered off
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-0fba594127a5476589f37299805023e4
Source dataset
uspto-grants-1996_01
Patent number
US05484928

Reaction notes

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