Anisole trifluoroacetic acid → HCID 178502773, compound

HRID 329930Notes

Reaction equation

HRID 329930 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:47]/[O:48][CH3:49])/[C:8]([NH:10][CH:11]2[C:45](=[O:46])[N:13]3[C:14]([C:42]([OH:44])=[O:43])=[C:15]([CH2:18][NH:19][C:20]4[N:21](C)[N:22]=[C:23](OC(C5C=CC=CC=5)C5C=CC=CC=5)[C:24](=[O:26])[N:25]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[C:50]1([O:56]C)C=CC=CC=1.C(O)(C(F)(F)F)=O>>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:47]/[O:48][CH3:49])/[C:8]([NH:10][CH:11]2[C:45](=[O:46])[N:13]3[C:14]([C:42]([OH:44])=[O:43])=[C:15]([CH2:18][NH:19][C:20]4[NH:21][N:22]=[C:23]([CH2:50][OH:56])[C:24](=[O:26])[N:25]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

3

Reactant 2

HCID 66633105Anisole trifluoroacetic acidHCID 177715839HCID 177715839, compound

Product 1

HCID 178502773HCID 178502773, compoundYield 25%

Procedure

A solution of 7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]-3-[(2,5-dihydro-6-diphenylmethoxy-2-methyl-5-oxo-1,2,4-triazin-3-yl)aminomethyl]ceph-3-em-4-carboxylic acid (400 mg.) in anisole/TFA (1:1 v/v; 10 ml.) was allowed to stand at ambient temperature for 20 minutes. The solvent was evaporated and the residue was dissolved in an aqueous ammonium carbonate buffer, pH6, and purified by HPLC using ammonium carbonate buffer/MeOH 92:8 v/v as eluant to give 7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]-3-[(2,5-dihydro-6-hydroxymethyl-5-oxo-1,2,4-triazin-3-yl)aminomethyl]ceph-3-em-4-carboxylic acid (yield 25%) having the following nmr in solvent B:--3.52(s,3 H); 3.6(s, 2 H); 4.04(s, 3 H); 4.4(s, 2 H); 5.18(d,1 H); 5.84(d, 1 H); 7.1(s, 1 H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in an aqueous ammonium carbonate buffer, pH6
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-6f57e2aaee6949b188c30940d487de51
Source dataset
uspto-grants-1990_01
Patent number
US04894371

Reaction notes

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