Trifluoroacetic acid → HCID 9985103, compound

HRID 569140Notes

Reaction equation

HRID 569140 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][CH2:19][C:18]=2[CH2:46][O:47][C:48](=[O:50])[NH2:49])=[O:16])C2C=CC=CC=2)C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>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])=[C:18]([CH2:46][O:47][C:48](=[O:50])[NH2:49])[CH2:19][S:20][C@H:21]23)=[O:44])[N:32]=1)=[O:38])([CH3:43])([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 9987417HCID 9987417, compound

Product 1

HCID 9985103HCID 9985103, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of 7beta-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl]amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid diphenylmethyl ester (855 mg), anisole (3.3 ml), and dichloromethane (8.3 ml) is added trifluoroacetic acid (1.93 ml) with stirring. After reacting at the same temperature for 30 minutes, the mixture is concentrated in vacuum. The residue is washed with petroleum ether and ether to give pale brown 7beta-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl]amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (640 mg).

Workup

  1. concentrationthe mixture is concentrated in vacuum
  2. washThe residue is washed with petroleum ether and ether

Sources & evidence

ORD record
ord-0af34fcb9d0048a987b67fee2afa5fca
Source dataset
uspto-grants-1988_03
Patent number
US04731361

Reaction notes

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