Methanol trifluoroacetic acid → (6R)-3-(aminomethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;2,2,2-trifluoroacetic acid

HRID 1722561Notes

Reaction equation

HRID 1722561 reaction equation
[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:15]([NH:16][C:17](=[O:28])/[C:18](/[C:22]3[N:23]=[C:24]([NH2:27])[S:25][CH:26]=3)=[N:19]\[O:20][CH3:21])[C:14](=[O:29])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12])=[N+]=[N-].CO.[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]>[Ni].CO>[F:35][C:34]([F:37])([F:36])[C:32]([OH:38])=[O:33].[NH2:1][CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:15]([NH:16][C:17](=[O:28])/[C:18](/[C:22]3[N:23]=[C:24]([NH2:27])[S:25][CH:26]=3)=[N:19]\[O:20][CH3:21])[C:14](=[O:29])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 86669916Methanol trifluoroacetic acidHCID 141548216(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(azidomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 88601873(6R)-3-(aminomethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;2,2,2-trifluoroacetic acidYield 45%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

To a stirred suspension of Raney nickel (16 g.) in MeOH (13 ml.) at 0° was added a solution of 3-azidomethyl-7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]ceph-3-em-4-carboxylic acid (2.96 g.) in MeOH/TFA (14 ml., 1.13 ml.). After effervescence ceased the mixture was diluted with MeOH and filtered through paper. The filtrate was evaporated, the residue purified by HPLC using water/HOAc/MeOH 79:1:20 v/v/v as eluant and the product dried over P2O5 to give 3-aminomethyl-7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]ceph-3-em-4-carboxylic acid trifluoroacetate (yield 45%) having the following n.m.r. in solvent A: 3.5-4.2 (m, 4H); 3.9 (s, 3H); 5.15 (d, 1H); 5.85 (d, 1H); 6.75 (s, 1H).

Workup

  1. filtrationfiltered through paper
  2. customThe filtrate was evaporated
  3. customthe residue purified by HPLC
  4. dry with materialthe product dried over P2O5

Sources & evidence

ORD record
ord-be51c0653b0048d0bd5e4442f2d351ee
Source dataset
uspto-grants-1989_08
Patent number
US04855420

Reaction notes

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