Ammonia → HCID 67834077, compound

HRID 1681457Notes

Reaction equation

HRID 1681457 reaction equation
C1(CC([NH:10][CH:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([OH:25])=[O:24])=[C:15](/[CH:18]=[CH:19]\[CH:20]4[CH2:22][CH2:21]4)[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.N.CC1(C)S[C@@H]2[C@H](NC(CC3C=CC=CC=3)=O)C(=O)N2[C@H]1C([O-])=O.[K+]>O>[NH2:10][CH:11]1[C:26](=[O:27])[N:13]2[C:14]([C:23]([OH:25])=[O:24])=[C:15](/[CH:18]=[CH:19]\[CH:20]3[CH2:22][CH2:21]3)[CH2:16][S:17][C@H:12]12

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 23664709Penicillin G PotassiumHCID 67834154HCID 67834154, compound

Product 1

HCID 67834077HCID 67834077, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
37 °C

Procedure

6 g (0.0156 mol) of 7-phenylacetamido-3-[(Z)-2-cyclopropyl-viny]-3-cephem-4-carboxylic acid are suspended in 320 ml of water and the suspension is brought to pH 7.8 with half-concentrated ammonia solution, whereupon an almost clear solution forms. The solution is warmed to 37° C. and 35 g of penicillin-acylase resin are added. The reaction solution is titrated further to pH 7.8 with ammonia and kept at 37° C. for 5 hours. The resin is then filtered off with suction and the filtrate is concentrated down to a volume of 50 ml. The concentrated solution is brought to pH 4.2 with 2N HCl, whereupon the product precipitates out and is filtered off with suction and washed with water and acetone.

Workup

  1. filtrationThe resin is then filtered off with suction
  2. concentrationthe filtrate is concentrated down to a volume of 50 ml
  3. customprecipitates out
  4. filtrationis filtered off with suction
  5. washwashed with water and acetone

Sources & evidence

ORD record
ord-eae6aee147a3404088d16fe5eae0c152
Source dataset
uspto-grants-1992_12
Patent number
US05171854

Reaction notes

Loading…