Hydrochloric Acid → Gemcitabine Hydrochloride

HRID 217106Notes

Reaction equation

HRID 217106 reaction equation
[CH:1]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[N:3]([C@@H:9]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C:10]2([F:18])[F:17])[CH:2]=1.[ClH:19]>O1CCOCC1>[CH:1]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[N:3]([C@@H:9]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C:10]2([F:17])[F:18])[CH:2]=1.[ClH:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60750Gemcitabine

Product 1

HCID 60749Gemcitabine Hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
12.5 °C

Procedure

To the 20 g of thick oil of Gemcitabine base obtained as in example 3 was added 1,4-Dioxane (120 ml) and the mixture was heated to 60°-68° C. and stirred for 15 minutes. Conc. HCl (10 ml) was then added to the mixture and the contents were heated at same temperature for one hour. Reaction mass was then cooled to 10-15° C. and maintained for 30 minutes. The solid thus obtained was filtered off and washed with 1,4-Dioxane and dried under vacuum at 55-60° C. to get 8 g material with Specific Optical Rotation i.e.[α]D=+40° and HPLC purity of 85% β-anomer and 8% α-anomer.

Workup

  1. temperaturethe mixture was heated to 60°-68° C.
  2. temperaturethe contents were heated at same temperature for one hour
  3. customReaction mass
  4. temperaturemaintained for 30 minutes
  5. customThe solid thus obtained
  6. filtrationwas filtered off
  7. washwashed with 1,4-Dioxane
  8. customdried under vacuum at 55-60° C.

Sources & evidence

ORD record
ord-e4b3723cf41e44089ee9b2568a14a59f
Source dataset
uspto-grants-2012_06
Patent number
US08193354B2

Reaction notes

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