Trifluoroacetic acid → HCID 178460195, compound

HRID 329935Notes

Reaction equation

HRID 329935 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:53]/[O:54][C:55]([C:58]([OH:60])=[O:59])([CH3:57])[CH3:56])/[C:15]([NH:17][CH:18]2[C:51](=[O:52])[N:20]3[C:21]([C:48]([OH:50])=[O:49])=[C:22]([CH2:25][NH:26][C:27]4[S:31][N:30]=[C:29]([O:32]C(C5C=CC=CC=5)C5C=CC=CC=5)[C:28]=4[C:46]#[N:47])[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1>C1(OC)C=CC=CC=1>[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:53]/[O:54][C:55]([C:58]([OH:60])=[O:59])([CH3:57])[CH3:56])/[C:15]([NH:17][CH:18]2[C:51](=[O:52])[N:20]3[C:21]([C:48]([OH:50])=[O:49])=[C:22]([CH2:25][NH:26][C:27]4[S:31][N:30]=[C:29]([OH:32])[C:28]=4[C:46]#[N:47])[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 88615306HCID 88615306, compound

Product 1

HCID 178460195HCID 178460195, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

TFA (2 ml) was added to a suspension of 7-[2-(2-aminothiazol-4-yl)-2-((Z)-1-carboxy-1-methylethoxyimino)acetamido]-3-(4-cyano-3-diphenylmethoxyisothiazol-5-yl)aminomethylceph-3-em-4-carboxylic acid (600 mg) in anisole (2 ml), and the mixture stirred for one hour at ambient temperature. The reaction mixture was evaporated and the residue purified by HPLC eluting with a mixture of MeOH and ammonium carbonate buffer 20:80 v/v. After lyophilisation the title compound was obtained in the form of its ammonium salt (49 mg). NMR in solvent B:--1.5 (s, 3 H); 3.4-3.6 (m, 2 H); 4.1-4.3 (m, 2 H); 5.15 (d, 1 H); 5.8 (d, 1 H); 7.0 (s, 1 H).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue purified by HPLC
  3. washeluting with a mixture of MeOH and ammonium carbonate buffer 20:80 v/v

Sources & evidence

ORD record
ord-436384d412c445ddbcbfec23ccc9e7cc
Source dataset
uspto-grants-1990_01
Patent number
US04894371

Reaction notes

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