Sodium Hydroxide → D-Pemetrexed disodium

HRID 706414Notes

Reaction equation

HRID 706414 reaction equation
[CH:1]1[C:6]([CH2:7][CH2:8][C:9]2[C:13]3[C:14]([NH:16][C:17]([NH2:19])=[N:18][C:12]=3[NH:11][CH:10]=2)=[O:15])=[CH:5][CH:4]=[C:3]([C:20]([NH:22][C@@H:23]([C:29]([OH:31])=[O:30])[CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:21])[CH:2]=1.[OH-].[Na+:33]>CCO>[CH:5]1[C:6]([CH2:7][CH2:8][C:9]2[C:13]3[C:14]([NH:16][C:17]([NH2:19])=[N:18][C:12]=3[NH:11][CH:10]=2)=[O:15])=[CH:1][CH:2]=[C:3]([C:20]([NH:22][C@@H:23]([C:29]([O-:31])=[O:30])[CH2:24][CH2:25][C:26]([O-:28])=[O:27])=[O:21])[CH:4]=1.[Na+:33].[Na+:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135565230Pemetrexed, (R)-

Product 1

HCID 135625269D-Pemetrexed disodium

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of Pemetrexed in EtOH containing 0% to 2% water (v/v) was heated to reflux and 2.0 eq of aq. NaOH (30% w/w) were added within 1 min. The mixture was stirred at reflux for 16 h before the suspension was cooled to 20° C. to 30° C. The solid was isolated by filtration, washed with EtOH and dried in vacuo to constant weight to give Pemetrexed Disodium Form A.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureat reflux for 16 h before the suspension
  4. temperaturewas cooled to 20° C. to 30° C
  5. customThe solid was isolated by filtration
  6. washwashed with EtOH
  7. customdried in vacuo to constant weight

Sources & evidence

ORD record
ord-c2ddad7f1edb4428a8880449a6d3860e
Source dataset
uspto-grants-2015_11
Patent number
US09174991B2

Reaction notes

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