Water → HCID 131715669, compound

HRID 34496Notes

Reaction equation

HRID 34496 reaction equation
O.C([NH:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[N:50][O:51][CH:52]([F:54])[F:53])[C:28]([NH:30][CH:31]2[C:48](=[O:49])[N:33]3[C:34]([C:45]([OH:47])=[O:46])=[C:35]([CH2:38][S:39][C:40]4[S:41][CH:42]=[N:43][N:44]=4)[CH2:36][S:37][C@H:32]23)=[O:29])[N:26]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)=O>[NH2:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[N:50][O:51][CH:52]([F:53])[F:54])[C:28]([NH:30][CH:31]2[C:48](=[O:49])[N:33]3[C:34]([C:45]([OH:47])=[O:46])=[C:35]([CH2:38][S:39][C:40]4[S:41][CH:42]=[N:43][N:44]=4)[CH2:36][S:37][C@H:32]23)=[O:29])[N:26]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 1317156677-[2-(2-Tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 131715669HCID 131715669, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Water (2.7 ml) was added to a stirred solution of 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.9 g) in formic acid (9 ml) at 7° C. under ice-cooling and the mixture was stirred at the same temperature for 4 hours. The reaction mixture was poured into a mixture of water (150 ml) and ethyl acetate (50 ml) and adjusted to pH 2.5 with an aqueous solution of sodium bicarbonate. The separated organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo to give 7-[2-(2-aminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.4 g).

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-2f783bb966eb4717bc395238bd5bf479
Source dataset
uspto-grants-1988_08
Patent number
US04761410

Reaction notes

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