Trifluoroacetic acid → HCID 131709919, compound

HRID 1580485Notes

Reaction equation

HRID 1580485 reaction equation
C(O[CH2:5][C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:27])[CH:16]([NH:17][C:18](=[O:26])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:9]2[S:8][CH:7]=1)(=O)C.[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>C1(C)C=CC=CC=1>[C:20]1([CH2:19][C:18]([NH:17][CH:16]2[C:15](=[O:27])[N:10]3[CH:11]([C:12]([OH:14])=[O:13])[C:6]([CH2:5][O:31][C:30](=[O:32])[C:29]([F:34])([F:33])[F:28])=[CH:7][S:8][C@H:9]23)=[O:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131709916HCID 131709916, compound

Product 1

HCID 131709919HCID 131709919, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.8 g of 3-acetoxymethyl-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid in 4 ml of trifluoroacetic acid is left to stand for 15 minutes at room temperature and is then diluted with an equal quantity of toluene. The volatile constituents are evaporated under reduced pressure and at room temperature. The residue is taken up in 100 ml of chloroform and the mixture is filtered. The filtrate is concentrated to a small volume under reduced pressure and cooled. The resulting solid material is filtered off and yields 7-(N-phenylacetyl-amino)-3-trifluoroacetoxymethyl-ceph-2-em-4ξ-carboxylic acid, melting at 139° - 140°C; infrared absorption spectrum (in mineral oil): characteristic bands at 3.01μ, 5.60μ, 5.65μ, 5.73μ, 5.77μ, 6.02μ and 6.54μ. A further quantity of the desired product can be obtained by further concentration and cooling of the filtrate.

Workup

  1. customThe volatile constituents are evaporated under reduced pressure and at room temperature
  2. filtrationthe mixture is filtered
  3. concentrationThe filtrate is concentrated to a small volume under reduced pressure
  4. temperaturecooled
  5. filtrationThe resulting solid material is filtered off

Sources & evidence

ORD record
ord-0b981e3e31f34bf9a83c00190a424f18
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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