Hydrochloric Acid → Tigecycline Hydrochloride

HRID 889674Notes

Reaction equation

HRID 889674 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(C(C)=O)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, compound

Product 1

HCID 54749425Tigecycline HydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

50.0 mg Tigecycline (Tygacil® 50 mg, Wyeth®, powder for infusion) were dissolved in 500 μl ethylmethylketone and the solution was stirred at room temperature. After about one minute an orange precipitate appeared (essentially pure form Ill). Afterwards 8.4 mg (1 eq) concentrated hydrochloric acid were added and the suspension was stirred for approximately 3 hours. The solid was filtered off, washed with ethylmethylketone and dried under vacuum at room temperature to obtain 43.7 mg (82% yield) of crystalline form A of Tigecycline hydrochloride.

Workup

  1. stirringthe suspension was stirred for approximately 3 hours
  2. filtrationThe solid was filtered off
  3. washwashed with ethylmethylketone
  4. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-995a81760a414019b7fbeef6778d002c
Source dataset
uspto-grants-2012_08
Patent number
US08252946B2

Reaction notes

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