Hydrochloric Acid → Gemcitabine Hydrochloride

HRID 217107

Reaction equation

HRID 217107 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]>C(COC)OC>[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 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
64 °C

Procedure

To the 20 g of thick oil of Gemcitabine base as obtained in example 3 was added Monoglyme (120 ml) and the mixture was heated at 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 is filtered off and washed with Monoglyme and dried under vacuum at 55-60° C. to get 8 g material having HPLC purity with 85% β-anomer & 9% α-anomer, Specific Optical Rotation i.e.[α]D=+40°

Workup

  1. temperaturethe contents were heated at same temperature for one hour
  2. customReaction mass
  3. temperaturewas then cooled to 10-15° C.
  4. temperaturemaintained for 30 minutes
  5. customThe solid thus obtained
  6. filtrationis filtered off
  7. washwashed with Monoglyme
  8. customdried under vacuum at 55-60° C.

Sources & evidence

ORD record
ord-0c980c678b044690a140b96cba6b62f9
Source dataset
uspto-grants-2012_06
Patent number
US08193354B2

Linked notes

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