(Phenylthio)acetic acid → HCID 86757446, compound

HRID 1597698Notes

Reaction equation

HRID 1597698 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]1([S:19][CH2:20][C:21]([OH:23])=O)[CH:18]=[CH:17][CH:16]=[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:69])[N:47]([CH2:50][C:51]3[CH:56]=[CH:55][N+:54]([CH2:57][C:58](=[O:68])[NH:59][C:60]4[CH:65]=[CH:64][C:63]([OH:66])=[C:62]([F:67])[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>[F:67][C:62]1[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:13]5[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=5)[C:37]=4[C:41]([O-:43])=[O:42])/[C:46]3=[O:69])=[CH:52][CH:53]=2)=[O:68])[CH:65]=[CH:64][C:63]=1[OH:66]

Participants

5

Reactant 3

HCID 59541(Phenylthio)acetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 87846597HCID 87846597, compound

Product 1

HCID 86757446HCID 86757446, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

With 175.0 mg (1.08 mmol) 1,1′-carbonyldiimidazole, 182.0 mg (1.08 mmol) 2-(phenylthio)acetic acid and 500.0 mg (0.75 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 N,N-dimethylacetamide. The resulting 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). The organic solvent was stripped off at a rotary evaporator and the aqueous phase was freeze-dried.

Workup

  1. customThe resulting 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)
  2. customThe organic solvent was stripped off at a rotary evaporator
  3. customthe aqueous phase was freeze-dried

Sources & evidence

ORD record
ord-cf958d1f5ba7437fa816749bea540f81
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

Loading…