Trifluoroacetic acid → HCID 88649774, compound

HRID 569138Notes

Reaction equation

HRID 569138 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:45])[C@@H:24]([NH:25][C:26](=[O:44])/[C:27](/[C:31]4[N:32]=[C:33]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[S:34][CH:35]=4)=[CH:28]\[CH2:29][CH3:30])[C@H:21]3[S:20](=[O:46])[CH2:19][CH:18]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1.ClCCl>[C:40]([O:39][C:37]([NH:36][C:33]1[S:34][CH:35]=[C:31](/[C:27](=[CH:28]/[CH2:29][CH3:30])/[C:26]([NH:25][C@@H:24]2[C:23](=[O:45])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[CH:18][CH2:19][S:20](=[O:46])[C@H:21]23)=[O:44])[N:32]=1)=[O:38])([CH3:43])([CH3:42])[CH3:41]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 88650588HCID 88650588, compound

Product 1

HCID 88649774HCID 88649774, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of 7beta-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl]amino-3-cephem-4-carboxylic acid 1-oxide diphenylmethyl ester (265 mg) in a mixture of anisole (0.8 ml) and dichloromethane (1.5 ml) is added trifluoroacetic acid (1 ml) at 0° C. with stirring. After 45 minutes' stirring, the mixture is concentrated in vacuum. The residue is washed with petroleum ether and ether to give 7beta-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl]amino-3-cephem-4-carboxylic acid 1-oxide (180 mg).

Workup

  1. stirringAfter 45 minutes' stirring
  2. concentrationthe mixture is concentrated in vacuum
  3. washThe residue is washed with petroleum ether and ether

Sources & evidence

ORD record
ord-637eae2114e44d96bcf6766fa0f7aa0a
Source dataset
uspto-grants-1988_03
Patent number
US04731361

Reaction notes

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