Sodium Bicarbonate → HCID 131715217, compound

HRID 2118600Notes

Reaction equation

HRID 2118600 reaction equation
[NH2:1][CH:2]1[C:16](=[O:17])[N:4]2[C:5]([C:13]([OH:15])=[O:14])=[C:6]([CH2:9][N:10]=[N+:11]=[N-:12])[CH2:7][S:8][C@H:3]12.[C:18](=[O:21])(O)[O-:19].[Na+]>O.C(O)(C)(C)C>[N:10]([CH2:9][C:6]1[CH2:7][S:8][C@@H:3]2[CH:2]([NH:1][C:18]([O:19][C:6]([CH3:9])([CH3:7])[CH3:5])=[O:21])[C:16](=[O:17])[N:4]2[C:5]=1[C:13]([OH:15])=[O:14])=[N+:11]=[N-:12]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 128022197-Amino-3-azidomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 131715217HCID 131715217, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent3×

Procedure

7-Amino-3-azidomethylceph-3-em-4-carboxylic acid (170 g.) was suspended by stirring in water (750 ml.) and sodium bicarbonate (60 g.) added carefully, followed by t-butanol (750 ml.). Bis(O-t-butyl)carbonic anhydride (170 ml.) dissolved in t-butanol (375 ml.) was added and the mixture left to stir at ambient temperature; further portions of reagent (20 ml.) in t-butanol (40 ml.) were added after 24 and 48 hours. After 72 hours, t-butanol was removed by evaporation and the aqueous residue, diluted with water to 21°, was cooled in ice. The pH was reduced to 3 with concentrated hydrochloric acid, and the precipitate filtered, and washed free of acid. After drying under vacuum, the crude product was extracted successively with 500 ml. and two 400 ml. portions of acetonitrile. The combined extracts were evaporated to a small volume and filtered to give 3-azidomethyl-7-t-butoxycarbonylaminoceph-3-em-4-carboxylic acid (84 g.), having the following n.m.r. in solvent A: 1.4(s, 9 H); 3.5(d, 2H); 4.2(d, 2H); 5.0(d, 1H); 5.4(d, 1H).

Workup

  1. additionwas added
  2. waitthe mixture left
  3. customt-butanol was removed by evaporation
  4. additionthe aqueous residue, diluted with water to 21°
  5. temperaturewas cooled in ice
  6. filtrationthe precipitate filtered
  7. washwashed free of acid
  8. customAfter drying under vacuum
  9. extractionthe crude product was extracted successively with 500 ml
  10. customThe combined extracts were evaporated to a small volume
  11. filtrationfiltered

Sources & evidence

ORD record
ord-75d077a3c10842fe99e83f3952513d98
Source dataset
uspto-grants-1987_07
Patent number
US04678781

Reaction notes

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