Water → HCID 49863419, compound

HRID 1399504Notes

Reaction equation

HRID 1399504 reaction equation
O.[CH3:2][C:3]([O:8]/[N:9]=[C:10](\[C:17]([NH:19][C@@H:20]1[C:23](=[O:24])[N:22]2[C:25]([C:44]([OH:46])=[O:45])=[C:26]([CH2:29][N+:30]3[N:34]([CH3:35])[C:33]([NH2:36])=[C:32]([NH:37][C:38]([NH:40][CH2:41][CH2:42][NH2:43])=[O:39])[CH:31]=3)[CH2:27][S:28][C@H:21]12)=[O:18])/[C:11]1[N:12]=[C:13]([NH2:16])[S:14][N:15]=1)([C:5]([O-:7])=[O:6])[CH3:4].[S:47](=[O:51])(=[O:50])([OH:49])[OH:48]>C(O)(C)C>[CH3:4][C:3]([O:8]/[N:9]=[C:10](\[C:17]([NH:19][C@@H:20]1[C:23](=[O:24])[N:22]2[C:25]([C:44]([OH:46])=[O:45])=[C:26]([CH2:29][N+:30]3[N:34]([CH3:35])[C:33]([NH2:36])=[C:32]([NH:37][C:38]([NH:40][CH2:41][CH2:42][NH2:43])=[O:39])[CH:31]=3)[CH2:27][S:28][C@H:21]12)=[O:18])/[C:11]1[N:12]=[C:13]([NH2:16])[S:14][N:15]=1)([C:5]([O-:7])=[O:6])[CH3:2].[OH:50][S:47]([OH:51])(=[O:49])=[O:48]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 71457955689293-68-32×

Product 1

HCID 49863419HCID 49863419, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A ceftolozane sulfate composition can be obtained by a process comprising the steps of: (a) forming a solution comprising water, 72-100 g/L ceftolozane active and 1.5-2.95 molar equivalents of sulfuric acid to ceftolozane; (b) combining the solution from step (a) with 20-40 volumes of isopropyl alcohol added to the solution over 0.5-8 hours to obtain solid ceftolozane sulfate; and (c) isolating the solid ceftolozane sulfate from the solution. The temperature of the solution can be about 0-20 degrees C., preferably 8-12 degrees C. (e.g. 10 degrees C.). Optionally, the process can further include adding a ceftolozane sulfate seed crystal, preferably in an amount of 0.03-4.0% w/w and allowing the seed crystal to age in the solution for about 1-5 hours. Optionally, the process can include allowing the solution to age for up to about 8 hours after adding the isopropyl alcohol.

Workup

  1. customforming a solution
  2. additionadded to the solution over 0.5-8 hours

Sources & evidence

ORD record
ord-cd41226214584383926d0e404e2e4866
Source dataset
uspto-grants-2014_12
Patent number
US08906898B1

Reaction notes

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