Hydrochloric Acid → 7-[2-(2-propynyloxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-[1-(2-carboxy-2-methoxyiminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

HRID 904878Notes

Reaction equation

HRID 904878 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([C:37]1[N:38]=[C:39]([NH:42]C(=O)C(F)(F)F)[S:40][CH:41]=1)[C:7]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:32]([OH:34])=[O:33])=[C:14]([CH2:17][S:18][C:19]3[N:23]([CH2:24][C:25]([C:29]([OH:31])=[O:30])=[N:26][O:27][CH3:28])[N:22]=[N:21][N:20]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[C:2]#[CH:3].C([O-])(=O)C.[Na+].Cl>O>[CH2:1]([O:4][N:5]=[C:6]([C:37]1[N:38]=[C:39]([NH2:42])[S:40][CH:41]=1)[C:7]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:32]([OH:34])=[O:33])=[C:14]([CH2:17][S:18][C:19]3[N:23]([CH2:24][C:25]([C:29]([OH:31])=[O:30])=[N:26][O:27][CH3:28])[N:22]=[N:21][N:20]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 1317132457-[2-(2-propynyloxyimino)-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-[1-(2-carboxy-2-methoxyiminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317132497-[2-(2-propynyloxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-[1-(2-carboxy-2-methoxyiminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-[2-(2-propynyloxyimino)-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-[1-(2-carboxy-2-methoxyiminoethyl)-1H-tetrazol-5yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer: in the 7-position) (2.0 g) and sodium acetate.trihydrate (3.71 g) in water (15 ml) was stirred overnight at room temperature. The solution was adjusted to pH 2.5 with 10% hydrochloric acid under ice-cooling and the resultant precipitates were filtered and washed with water to give 7-[2-(2-propynyloxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-[1-(2-carboxy-2-methoxyiminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer: in the 7-position).(1.12 g).

Workup

  1. temperaturecooling
  2. customthe resultant precipitates
  3. filtrationwere filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-7eb94c73f49e45348d0d94136eb2b72e
Source dataset
uspto-grants-1983_12
Patent number
US04420477

Reaction notes

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