Hydrochloric Acid → (2S)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid

HRID 1670686Notes

Reaction equation

HRID 1670686 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O:14][C:15](=[O:46])[C@H:16]([CH2:39][CH2:40][C:41]([O:43]CC)=[O:42])[NH:17][C:18](=[O:38])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]2[C:35]3[C:34](=[O:36])[N:33]=[C:32]([NH2:37])[NH:31][C:30]=3[NH:29][CH:28]=2)=[CH:21][CH:20]=1)C.O.Cl>[OH-].[Na+]>[NH2:37][C:32]1[NH:31][C:30]2[NH:29][CH:28]=[C:27]([CH2:26][CH2:25][C:22]3[CH:21]=[CH:20][C:19]([C:18]([NH:17][C@H:16]([C:15]([OH:46])=[O:14])[CH2:39][CH2:40][C:41]([OH:43])=[O:42])=[O:38])=[CH:24][CH:23]=3)[C:35]=2[C:34](=[O:36])[N:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178471564HCID 178471564, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

N-(4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl)-L-glutamic acid diethyl ester p-toluenesulfonic acid salt (1.0 g) is dissolved in 6.7 mL aqueous sodium hydroxide and stirred until complete solution is obtained. 6 mL of water is added and the pH is adjusted to 3.0-3.5 by the addition of diluted hydrochloride acid. The resulting slurry is heated at 70° C. for an hour and then filtered to yield the title compound in 99.6% purity (HPLC).

Workup

  1. customis obtained
  2. filtrationfiltered

Sources & evidence

ORD record
ord-eddb4902adc34a139268e847d8297155
Source dataset
uspto-grants-2011_08
Patent number
US07994180B2

Reaction notes

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