Hydrochloric Acid → HCID 86757442, compound

HRID 1597696Notes

Reaction equation

HRID 1597696 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: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].Cl>CN(C)C(=O)C.O.C(#N)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: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:68])=[CH:52][CH:53]=2)=[O:67])=[CH:65][CH:64]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 59541(Phenylthio)acetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 86757436HCID 86757436, compound

Product 1

HCID 86757442HCID 86757442, compound

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

With 70.0 mg (0.43 mmol) 1,1′-carbonyldiimidazole, 71.0 mg (0.43 mmol) 2-(phenylthio)acetic acid and 188.4 mg (0.29 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 resulting solid was suspended in 6 ml water:acetonitrile (1:1) and HCl was added until all compound dissolved. After column chromatography on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water:acetonitril (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. dissolutiondissolved
  2. customAfter column chromatography on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water:acetonitril (1:0, 4:1, 3:1, 2:1, 1:1) the organic solvent was stripped off at a rotary evaporator
  3. customthe aqueous phase was freeze-dried

Sources & evidence

ORD record
ord-ed79fec8c4af42dd9897a01ce26ec51b
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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