Water → HCID 13127783, compound

HRID 236218Notes

Reaction equation

HRID 236218 reaction equation
C(N(CCCC)CCCC)CCC.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:19][C:20]([NH:22][C@@H:23]1[C:35](=[O:36])[N:25]2[C:26]([C:32]([OH:34])=[O:33])=[C:27]([CH2:30]O)[CH2:28][S:29][C@H:24]12)=[O:21].[SH:37][C:38]1[N:42]([CH3:43])[N:41]=[N:40][N:39]=1.O>C(OCC)(=O)C>[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:19][C:20]([NH:22][C@@H:23]1[C:35](=[O:36])[N:25]2[C:26]([C:32]([OH:34])=[O:33])=[C:27]([CH2:30][S:37][C:38]3[N:42]([CH3:43])[N:41]=[N:40][N:39]=3)[CH2:28][S:29][C@H:24]12)=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 70378458HCID 70378458, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 13127783HCID 13127783, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
-20 °C

Procedure

To 10 ml of ethyl acetate were added 0.540 g of 7β-(2-thienylacetamido)-3-hydroxymethyl-3-cephem-4-carboxylic acid tri-n-butylamine salt and 0.175 g of 5-mercapto-1-methyl-1H tetrazole and, under cooling at -20° C. and stirring, a solution of 0.370 g of methyl o-phenylene phosphorochloridate in 5 ml of ethyl acetate was added. The mixture was stirred under ice-cooling for 1.5 hours and 10 ml of water was added. After phase separation, 20 ml of water was added to the organic layer and the mixture was adjusted to pH 9.0. The aqueous layer was taken and washed with 5 ml of ethyl acetate. To the aequous layer was added 20 ml of ethyl acetate and the mixture was adjusted to pH 2.0. After phase separation, the organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was distilled off under reduced pressure and ether was added. The powdery precipitate was collected by filtration to give 0.380 g (yield 84.1%) of 7β-(2-thienylacetamido)-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid. The IR and NMR spectra of this product were identical with those of the authentic sample.

Workup

  1. stirringThe mixture was stirred under ice-
  2. temperaturecooling for 1.5 hours
  3. customAfter phase separation, 20 ml of water
  4. additionwas added to the organic layer
  5. washwashed with 5 ml of ethyl acetate
  6. additionTo the aequous layer was added 20 ml of ethyl acetate
  7. customAfter phase separation
  8. washthe organic layer was washed with saturated aqueous sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe ethyl acetate was distilled off under reduced pressure and ether
  11. additionwas added
  12. filtrationThe powdery precipitate was collected by filtration

Sources & evidence

ORD record
ord-99d7379b852643448ef04fc9156addcb
Source dataset
uspto-grants-1987_02
Patent number
US04642365

Reaction notes

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