Sodium Hydroxide → D-Pemetrexed disodium

HRID 706408Notes

Reaction equation

HRID 706408 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]>O>[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 962WaterSolvent

Procedure

All routes start with saponification of Pemetrexed IM8 in water at IT=20° C. to 30° C. using 3.25 eq of NaOH. Upon complete conversion an aqueous solution of Pemetrexed Disodium with a pH of 13.0 to 13.5 is obtained. Starting from this mixture the desired route can be accessed by addition of HCl to adjust the pH to a certain value (depending on the route, FIG. 20).

Workup

  1. customat IT=20° C. to 30° C.

Sources & evidence

ORD record
ord-b51365021ac142809640108897f1237a
Source dataset
uspto-grants-2015_11
Patent number
US09174991B2

Reaction notes

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