Triethylamine → HCID 86757456, compound

HRID 1597706Notes

Reaction equation

HRID 1597706 reaction equation
Br[CH2:2][C:3]([NH:5][C@@H:6]1[C:13](=[O:14])[N:12]2[C@@H:7]1[S:8][CH2:9][C:10](/[CH:18]=[C:19]1/[C:20](=[O:43])[N:21]([CH2:24][C:25]3[CH:30]=[CH:29][N+:28]([CH2:31][C:32](=[O:42])[NH:33][C:34]4[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([F:41])[CH:35]=4)=[CH:27][CH:26]=3)[CH2:22][CH2:23]/1)=[C:11]2[C:15]([O-:17])=[O:16])=[O:4].[SH:44][C:45]1[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=1.C(N(CC)CC)C>CN(C)C=O>[F:41][C:36]1[CH:35]=[C:34]([NH:33][C:32]([CH2:31][N+:28]2[CH:27]=[CH:26][C:25]([CH2:24][N:21]3[CH2:22][CH2:23]/[C:19](=[CH:18]\[C:10]4[CH2:9][S:8][C@H:7]5[N:12]([C:13](=[O:14])[C@H:6]5[NH:5][C:3](=[O:4])[CH2:2][S:44][C:45]5[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=5)[C:11]=4[C:15]([O-:17])=[O:16])/[C:20]3=[O:43])=[CH:30][CH:29]=2)=[O:42])[CH:39]=[CH:38][C:37]=1[OH:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2401474-MercaptophenolHCID 86757452HCID 86757452, compound

Product 1

HCID 86757456HCID 86757456, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-(6R,7R)-7-(2-bromo-acetylamino)-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 (see ex. C1a) (300.0 mg, 0.45 mmol) was dissolved in 3 ml N,N-dimethylformamide, then 4-mercaptophenol (58.0 mg, 0.45 mmol), followed by triethylamine (62.7 ml, 0.45 mmol) was added. After 22 h the reaction mixture was poured on diethyl ether and the solid was collected by filtration. The brown solid material was suspended in water: acetonitrile (1:1) and chromatographed on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water: acetonitrile (9:1, 4:1, 3:1). The organic solvent was stripped off at a rotary evaporator and the aqueous phase was freeze-dried.

Workup

  1. additionwas added
  2. additionAfter 22 h the reaction mixture was poured on diethyl ether
  3. filtrationthe solid was collected by filtration
  4. customchromatographed on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water: acetonitrile (9:1, 4:1, 3:1)
  5. customThe organic solvent was stripped off at a rotary evaporator
  6. customthe aqueous phase was freeze-dried

Sources & evidence

ORD record
ord-6b89eb1900e74745bc74dd346db5f912
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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