Hydrochloric Acid → Tigecycline Hydrochloride

HRID 889673Notes

Reaction equation

HRID 889673 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: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, compound

Product 1

HCID 54749425Tigecycline HydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

50.0 mg Tigecycline (Tygacil® 50 mg, Wyeth, powder for infusion) were dissolved in 1 ml acetone and the solution was stirred at room temperature. After about one minute an orange precipitate appeared (form VI). Afterwards 8.4 mg (1 eq) concentrated hydrochloric acid were added and the suspension was stirred at room temperature. The colour of the suspension changed after about 5 minutes from orange to yellow and the suspension was stirred for 2.5 hours at room temperature. The solid was filtered off, washed with acetone and dried under vacuum at room temperature to obtain 51.8 mg (98% yield) of crystalline form A of Tigecycline hydrochloride.

Workup

  1. stirringthe suspension was stirred at room temperature
  2. waitThe colour of the suspension changed after about 5 minutes
  3. stirringfrom orange to yellow and the suspension was stirred for 2.5 hours at room temperature
  4. filtrationThe solid was filtered off
  5. washwashed with acetone
  6. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-8f60090c840347bba601a8ff4dfba2a9
Source dataset
uspto-grants-2012_08
Patent number
US08252946B2

Reaction notes

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