Hydrochloric Acid → Tigecycline Hydrochloride

HRID 889675Notes

Reaction equation

HRID 889675 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(Cl)Cl>[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 6344DichloromethaneSolvent

Procedure

A suspension of Tigecycline was prepared by mixing a solid Tigecycline sample and methylenchloride in amounts as shown in Table C. The mixture was than stirred at room temperature and 5N hydrochloric acid was added in amounts corresponding to Table C. After stirring for about 92 hours the solid was filtered off and dried at room temperature under vacuum to obtain crystalline form B of Tigecycline hydrochloride.

Workup

  1. customwas prepared
  2. stirringAfter stirring for about 92 hours the solid
  3. filtrationwas filtered off
  4. customdried at room temperature under vacuum

Sources & evidence

ORD record
ord-efcd4cc59246415493b9d6c0ad6fb70b
Source dataset
uspto-grants-2012_08
Patent number
US08252946B2

Reaction notes

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