1,1'-Carbonyldiimidazole → HCID 86757440, compound

HRID 1597695Notes

Reaction equation

HRID 1597695 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[N:13]1[CH:18]=[CH:17][C:16]([S:19][CH2:20][C:21]([OH:23])=O)=[CH:15][CH:14]=1.FC(F)(F)C([O-])=O.[NH2:31][C@@H:32]1[C:39](=[O:40])[N:38]2[C@@H:33]1[S:34][CH2:35][C:36](/[CH:44]=[C:45]1/[C:46](=[O:68])[N:47]([CH2:50][C:51]3[CH:56]=[CH:55][N+:54]([CH2:57][C:58](=[O:67])[NH:59][C:60]4[CH:65]=[CH:64][C:63]([OH:66])=[CH:62][CH:61]=4)=[CH:53][CH:52]=3)[CH2:48][CH2:49]/1)=[C:37]2[C:41]([OH:43])=[O:42]>CN(C)C(=O)C>[OH:66][C:63]1[CH:62]=[CH:61][C:60]([NH:59][C:58]([CH2:57][N+:54]2[CH:55]=[CH:56][C:51]([CH2:50][N:47]3[CH2:48][CH2:49]/[C:45](=[CH:44]\[C:36]4[CH2:35][S:34][C@H:33]5[N:38]([C:39](=[O:40])[C@H:32]5[NH:31][C:21](=[O:23])[CH2:20][S:19][C:16]5[CH:15]=[CH:14][N:13]=[CH:18][CH:17]=5)[C:37]=4[C:41]([O-:43])=[O:42])/[C:46]3=[O:68])=[CH:52][CH:53]=2)=[O:67])=[CH:65][CH:64]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 82574(4-Pyridylthio)acetic acidHCID 86757436HCID 86757436, compound

Product 1

HCID 86757440HCID 86757440, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

With 70.0 mg (0.43 mmol) 1,1′-carbonyldiimidazole, 72.8 mg (0.43 mmol) (pyridin-4-ylsulfanyl)-acetic acid and 232.8 mg (0.36 mmol) (E)-(6R,7R)-7-amino-3-[1-[1-[(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 ml N,N-dimethylacetamide. The brown solid was purified by column chromatography on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water: acetonitrile (1:0, 4:1, 3:1, 2:1, 1:1). The organic solvent was stripped off at a rotary evaporator and the aqueous phase was freeze-dried.

Workup

  1. customThe brown solid was purified by column chromatography on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water: acetonitrile (1:0, 4:1, 3:1, 2:1, 1:1)
  2. customThe organic solvent was stripped off at a rotary evaporator
  3. customthe aqueous phase was freeze-dried

Sources & evidence

ORD record
ord-b9cb2bacfe7649ccbc0fb79e6ffbe53e
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

Loading…