HCID 131710309, compound → HCID 131710308, compound

HRID 328075Notes

Reaction equation

HRID 328075 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][C@H:14]2[C:29](=[O:30])[N:16]3[C:17]([C:26]([O-:28])=[O:27])=[C:18]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:19][S:20][C@H:15]23)=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]>FC(F)(F)C(O)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][C@H:14]2[C:29](=[O:30])[N:16]3[C:17]([C:26]([OH:28])=[O:27])=[C:18]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:19][S:20][C@H:15]23)=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 131710309HCID 131710309, compound

Product 1

HCID 131710308HCID 131710308, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 244 mg of the ester of Step A in 2.5 ml of trifluoroacetic acid stood at room temperature for 8 minutes and was then evaporated to dryness under reduced pressure. The residue was taken up in benzene and was evaporated to dryness. The residue was triturated with ether and crystallization was effected. The crystals were vacuum filtered, washed with ether and dried to obtain 174 mg of DL cis 7-p-nitrophenylacetamido-3-cyclopentyl-3-cepheme-4-carboxylic acid melting at 170° C. The product occurred as colorless crystals slightly soluble in ethanol and insoluble in ether and water.

Workup

  1. customwas then evaporated to dryness under reduced pressure
  2. customwas evaporated to dryness
  3. customThe residue was triturated with ether and crystallization
  4. filtrationfiltered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-fa4666559c6a49938e1a605ef405ce65
Source dataset
uspto-grants-1977_04
Patent number
US04016158

Reaction notes

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