Sodium Hydroxide → HCID 178508844, compound

HRID 469268Notes

Reaction equation

HRID 469268 reaction equation
[NH2:1][C:2]1[NH:7][C:6]2[NH:8][CH:9]=[C:10]([CH2:11][CH2:12][C:13]3[CH:30]=[CH:29][C:16]([C:17]([NH:19][C@H:20]([C:26]([OH:28])=[O:27])[CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:18])=[CH:15][CH:14]=3)[C:5]=2[C:4](=[O:31])[N:3]=1.[OH-].[Na+:33]>O>[Na+:33].[Na+:33].[NH2:1][C:2]1[NH:7][C:6]2[NH:8][CH:9]=[C:10]([CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][C:16]([C:17]([NH:19][C@H:20]([C:26]([O-:28])=[O:27])[CH2:21][CH2:22][C:23]([O-:25])=[O:24])=[O:18])=[CH:29][CH:30]=3)[C:5]=2[C:4](=[O:31])[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 178508842(2S)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid2×

Product 1

HCID 178508844HCID 178508844, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.5 grams of N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid (purity 99.6% by HPLC) were dissolved in 0.5 L of distilled water with the addition of 5.849 mL of a 2.0M standard solution of sodium hydroxide. The pH of the solution was adjusted to 7.14 by adding a diluted solution of sodium hydroxide in water and a suspension of N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid in the same solvent. The obtained solution was dried in a freeze-drier affording the title compound as a white solid (2.8 g, purity 99.6% area by HPLC). Acidimetric titrations of the final product confirmed the absence of residual sodium hydroxide and pemetrexed diacid.

Workup

  1. customThe obtained solution was dried in a freeze-drier

Sources & evidence

ORD record
ord-eec395796b654724b111f3418e349bae
Source dataset
uspto-grants-2014_01
Patent number
US08629152B2

Reaction notes

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