Ammonia → HCID 11391647, compound

HRID 1283146Notes

Reaction equation

HRID 1283146 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C@@H:13]1[C:41](=[O:42])[N:15]2[C:16]([C:25]([O:27]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:26])=[C:17]([CH2:20][O:21][C:22](=[O:24])[NH2:23])[CH2:18][S:19][C@H:14]12.C(Cl)(Cl)Cl.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.N>O.C(OCC)(=O)C>[NH2:12][C@@H:13]1[C:41](=[O:42])[N:15]2[C:16]([C:25]([OH:27])=[O:26])=[C:17]([CH2:20][O:21][C:22](=[O:24])[NH2:23])[CH2:18][S:19][C@H:14]12

Participants

8

Reactant 5

HCID 222AmmoniaHCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 13127405HCID 13127405, compound

Product 1

HCID 11391647HCID 11391647, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diphenylmethyl (6R,7R)-7-amino-3-carbamoyloxymethylceph-3-em-4-carboxylate toluene-p-sulphonic acid salt (300.0 g, 0.44 mole), solvated with ca. 0.6 mole of chloroform, was added in portions over 30 minutes to a stirred mixture of trifluoroacetic acid (300 ml) and anisole (300 ml) immersed in a water-bath at 20°. The temperature of the mixture rose from 23° to 28° over the first 20 minutes but fell back to 26° by the end of the addition. The golden yellow solution was stirred for 1 hour, the temperature falling to 21°, and was then added to a stirred mixture of ethyl acetate (1.5 liters) and water (1.5 liters) immersed in an ice-bath. The pH of the stirred mixture was adjusted to 3.8 over 10 minutes with ammonia solution (S.G. 0.880), the temperature rising to 38°. The suspension was stirred and cooled to 10° over 1.25 hours and filtered. The cream solid was washed with water (750 ml) and ethyl acetate (4 × 200 ml) and dried in vacuo to give the title compound (115.6 g, 96.2%); λmax (pH6 phosphate) 265nm (ε7,750); purity by HPLC (high pressure liquid chromatography) 99.7%.

Workup

  1. customimmersed in a water-bath at 20°
  2. customrose from 23° to 28° over the first 20 minutes
  3. additionfell back to 26° by the end of the addition
  4. customfalling to 21°
  5. customimmersed in an ice-bath
  6. customrising to 38°
  7. stirringThe suspension was stirred
  8. temperaturecooled to 10° over 1.25 hours
  9. filtrationfiltered
  10. washThe cream solid was washed with water (750 ml) and ethyl acetate (4 × 200 ml)
  11. customdried in vacuo

Sources & evidence

ORD record
ord-b272c3f8b7524dbab6e2bf8cef5ad7d2
Source dataset
uspto-grants-1976_08
Patent number
US03974153

Reaction notes

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