Hydrochloric Acid → Tigecycline Hydrochloride

HRID 889671Notes

Reaction equation

HRID 889671 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]>C(#N)C>[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178482955HCID 178482955, compound2×

Product 1

HCID 54749425Tigecycline Hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of Tigecycline was prepared by mixing a solid Tigecycline sample and acetonitrile in amounts as shown in Table B. The mixture was than stirred for about 1 hour at room temperature before concentrated hydrochloric acid was added in amounts corresponding to Table B. After stirring for about 4 hours the solid was filtered off and dried at room temperature under vacuum to obtain crystalline form A of Tigecycline hydrochloride.

Workup

  1. customwas prepared
  2. additionwas added in amounts corresponding to Table B
  3. filtrationwas filtered off
  4. customdried at room temperature under vacuum

Sources & evidence

ORD record
ord-76bdddfb119d43868d7400c398f6af64
Source dataset
uspto-grants-2012_08
Patent number
US08252946B2

Reaction notes

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