Sodium Hydroxide → HCID 178508844, compound

HRID 469269Notes

Reaction equation

HRID 469269 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.C(O)(C)(C)C>[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

5

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 2

HCID 962WaterSolvent3×HCID 6386tert-ButanolSolvent

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% HPLC) were dissolved in a mixture of 0.3 L of distilled water and 0.2 L of t-butanol with the addition of 5.849 mL of a 2.0M standard solution of sodium hydroxide in water. 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 (2.7 g, purity 99.6% area by HPLC). Acidimetric titrations of the final product can be used to confirm 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-476b49e03e7f4bda8ccfac4778bdde16
Source dataset
uspto-grants-2014_01
Patent number
US08629152B2

Reaction notes

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