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

HRID 255791Notes

Reaction equation

HRID 255791 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:35][O:36][CH2:37][CH2:38][Cl:39])[C:10]([NH:12][CH:13]2[C:33](=[O:34])[N:15]3[C:16]([C:30]([OH:32])=[O:31])=[C:17]([CH2:20][S:21][C:22]4[N:26]([CH2:27][CH:28]=[CH2:29])[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:35][O:36][CH2:37][CH2:38][Cl:39])[C:10]([NH:12][CH:13]2[C:33](=[O:34])[N:15]3[C:16]([C:30]([OH:32])=[O:31])=[C:17]([CH2:20][S:21][C:22]4[N:26]([CH2:27][CH:28]=[CH2:29])[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317153227-[2-(2-formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317153237-[2-(2-aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidYield 60.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

A suspension of 7-[2-(2-formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 0.75 g.) and conc. hydrochloric acid (0.3 g.) in methanol (5.25 ml.) was stirred at 30° C. for 3 hours. After removing the solvent in vacuo, ethyl acetate and water were added to the residue and adjusted to pH 7.0 with sodium bicarbonate. The aqueous solution was separated, washed with ethyl acetate and adjusted to pH 3.0 with 10% hydrochloric acid. The ethyl acetate layer was separated, washed with a sodium chloride saturated aqueous solution, dried over magnesium sulfate and evaporated in vacuo. The residue was pulverized with diisopropyl ether. The precipitates were collected by filtration, washed with diisopropyl ether and dried to give 7-[2-(2-aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 0.43 g.).

Workup

  1. customAfter removing the solvent in vacuo, ethyl acetate and water
  2. additionwere added to the residue
  3. customThe aqueous solution was separated
  4. washwashed with ethyl acetate
  5. customThe ethyl acetate layer was separated
  6. washwashed with a sodium chloride saturated aqueous solution
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. filtrationThe precipitates were collected by filtration
  10. washwashed with diisopropyl ether
  11. customdried

Sources & evidence

ORD record
ord-fcda53ed2e2b4e8e93d988c8af8b3199
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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