Hydrochloric Acid → Tigecycline Hydrochloride

HRID 889672Notes

Reaction equation

HRID 889672 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([N:40]([CH3:42])[CH3:41])[C:13]2[CH2:25][C@@H:24]3[C:19](=[C:20]([OH:39])[C@:21]4([OH:38])[C:29](=[O:30])[C:28]([C:31]([NH2:33])=[O:32])=[C:27]([OH:34])[C@@H:26]([N:35]([CH3:37])[CH3:36])[C@@H:22]4[CH2:23]3)[C:17](=[O:18])[C:14]=2[C:15]=1[OH:16])=[O:8])([CH3:4])[CH3:3].[ClH:43]>CC(C)=O>[CH3:4][C:2]([NH:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([N:40]([CH3:42])[CH3:41])[C:13]2[CH2:25][C@@H:24]3[C:19](=[C:20]([OH:39])[C@:21]4([OH:38])[C:29](=[O:30])[C:28]([C:31]([NH2:33])=[O:32])=[C:27]([OH:34])[C@@H:26]([N:35]([CH3:37])[CH3:36])[C@@H:22]4[CH2:23]3)[C:17](=[O:18])[C:14]=2[C:15]=1[OH:16])=[O:8])([CH3:1])[CH3:3].[CH3:4][C:2]([NH:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([N:40]([CH3:42])[CH3:41])[C:13]2[CH2:25][C@@H:24]3[C:19](=[C:17]([OH:18])[C:14]=2[C:15]=1[OH:16])[C:20](=[O:39])[C@@:21]1([OH:38])[C@H:22]([C@H:26]([N:35]([CH3:36])[CH3:37])[C:27]([C:28]([C:31]([NH2:33])=[O:32])=[C:29]1[OH:30])=[O:34])[CH2:23]3)=[O:8])([CH3:1])[CH3:3].[ClH:43]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178482955HCID 178482955, compound

Product 2

HCID 54749425Tigecycline HydrochlorideYield 98.73%HCID 178482955HCID 178482955, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of Tigecycline was prepared by mixing 500 mg of a solid Tigecycline sample with 10 ml acetone. Within about 5 minutes a precipitate appeared and the suspension was further stirred for 1.75 h. 143 μl (1.0 mol equivalent) 5N hydrochloric acid were added to the suspension and stirring was continued for 5 hours. Finally the solid was filtered off, washed with acetone and dried at room temperature under vacuum to obtain 440 mg (97% yield) of crystalline form A of Tigecycline hydrochloride (98.73% purity by HPLC).

Workup

  1. stirringstirring
  2. waitwas continued for 5 hours
  3. filtrationFinally the solid was filtered off
  4. washwashed with acetone
  5. customdried at room temperature under vacuum

Sources & evidence

ORD record
ord-6a4eb31d163142658c31d202651a6e7a
Source dataset
uspto-grants-2012_08
Patent number
US08252946B2

Reaction notes

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