Water → HCID 86757452, compound

HRID 1597704Notes

Reaction equation

HRID 1597704 reaction equation
FC(F)(F)C([O-])=O.[NH2:8][C@@H:9]1[C:16](=[O:17])[N:15]2[C@@H:10]1[S:11][CH2:12][C:13](/[CH:21]=[C:22]1/[C:23](=[O:46])[N:24]([CH2:27][C:28]3[CH:33]=[CH:32][N+:31]([CH2:34][C:35](=[O:45])[NH:36][C:37]4[CH:42]=[CH:41][C:40]([OH:43])=[C:39]([F:44])[CH:38]=4)=[CH:30][CH:29]=3)[CH2:25][CH2:26]/1)=[C:14]2[C:18]([OH:20])=[O:19].C[Si](N=C(O[Si](C)(C)C)C(F)(F)F)(C)C.[Br:62][CH2:63][C:64](Br)=[O:65].O>ClCCl.C(OCC)C>[Br:62][CH2:63][C:64]([NH:8][C@@H:9]1[C:16](=[O:17])[N:15]2[C@@H:10]1[S:11][CH2:12][C:13](/[CH:21]=[C:22]1/[C:23](=[O:46])[N:24]([CH2:27][C:28]3[CH:29]=[CH:30][N+:31]([CH2:34][C:35](=[O:45])[NH:36][C:37]4[CH:42]=[CH:41][C:40]([OH:43])=[C:39]([F:44])[CH:38]=4)=[CH:32][CH:33]=3)[CH2:25][CH2:26]/1)=[C:14]2[C:18]([O-:20])=[O:19])=[O:65]

Participants

7

Reactant 4

HCID 962WaterHCID 61147Bromoacetyl bromideHCID 94358Bis(trimethylsilyl)trifluoroacetamideHCID 87846597HCID 87846597, compound

Product 1

HCID 86757452HCID 86757452, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 280.0 mg (0.42 mmol) (E)-(6R,7R)-7-amino-3-[1-[1-[(3-fluoro-4-hydroxy-phenylcarbamoyl)-methyl]-pyridin-1-ium-4-ylmethyl]-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate trifluoroacetate in 4 ml dichloromethane were added 0.37 μl (1.40 mmol) N,O-bis-(trimethylsilyl)-trifluoroacetamide. After a clear solution had formed, 36.8 μl (0.42 mmol) bromoacetyl bromide were added and the reaction mixture was stirred for 3 h. To this solution 25.6 μl (1.42 mmol) water and 25 ml diethyl ether was added. The precipitate was filtered off and washed with diethyl ether.

Workup

  1. customAfter a clear solution had formed
  2. filtrationThe precipitate was filtered off
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-b386227a460045d0a607f4b927814d40
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

Loading…