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Trifluoroacetic acid → Benzylamine

HRID 372869
Notes
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Reaction equation

HRID 372869 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[C:13]([C:23]([O:25]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:24])=[C:14]([CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8].[C:41]1(OC)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.F[C:50](F)(F)[C:51](O)=O.C(O[CH2:60][CH3:61])(=O)C>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[C:13]([C:23]([OH:25])=[O:24])=[C:14]([CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8].[N:9]1[C:10]([CH3:39])=[CH:11][C:60]([CH3:61])=[CH:41][C:51]=1[CH3:50].[CH2:7]([NH2:9])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 8857Ethyl AcetateHCID 70617769Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate

Product 3

HCID 7504BenzylamineHCID 79532,4,6-Trimethylpyridine
HCID 70617649
7-(2-Thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate (stereoisomer A: 58 mg) in methylene chloride (0.6 ml) are added anisole (0.12 ml) and trifluoroacetic acid (0.12 ml). After 15 minutes, the reaction mixture is concentrated at room temperature, and obtained residue is dissolved in ethyl acetate, and is extracted with aqueous sodium hydrogen carbonate solution. The extract aqueous solution is cooled with ice, stirred and neutralized with 1N-hydrochloric acid to pH 2, and is extracted with ethyl acetate. The extract solution is washed with water, dried over sodium sulfate, and concentrated to one third volume. To this solution is added an equivalent amount of collidine or benzylamine, and the separated crystals are collected by filtration to give 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylic acid (stereoisomer A) collidine salt or benzylamine salt.

Workup

  1. concentrationthe reaction mixture is concentrated at room temperature
  2. customobtained residue
  3. extractionis extracted with aqueous sodium hydrogen carbonate solution
  4. temperatureThe extract aqueous solution is cooled with ice
  5. extractionis extracted with ethyl acetate
  6. washThe extract solution is washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to one third volume
  9. additionTo this solution is added an equivalent amount of collidine or benzylamine
  10. filtrationthe separated crystals are collected by filtration

Sources & evidence

ORD record
ord-a9bba55a220144469d034be47b5d4100
Source dataset
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04092474

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes