Acetic Acid → HCID 178508851, compound

HRID 1494619Notes

Reaction equation

HRID 1494619 reaction equation
C([NH:4][C:5]1[N:6]=[C:7]([OH:39])[C:8]2[CH:14]=[C:13]([CH2:15][CH2:16][C:17]3[CH:38]=[CH:37][C:20]([C:21]([NH:23][C@H:24]([C:32]([O:34]CC)=[O:33])[CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])=[O:22])=[CH:19][CH:18]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=O)C.[OH-].[Na+].C(O)(=O)C>CO>[NH2:4][C:5]1[N:6]=[C:7]([OH:39])[C:8]2[CH:14]=[C:13]([CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([NH:23][C@H:24]([C:32]([OH:34])=[O:33])[CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:22])=[CH:37][CH:38]=3)[CH:12]=[N:11][C:9]=2[N:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 178471556HCID 178471556, compound

Product 1

HCID 178508851HCID 178508851, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A homogeneous solution of 0.175 of diethyl N-(4-[2-(2-acetamido-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-L-glutamate in 50 mL of methanol containing 3 mL of 1N aqueous sodium hydroxide was stirred at room temperature for 72 hours. Addition of 2 mL of acetic acid followed by centrifugation gave 0.125 g (86%) of the title compound, which can be alternatively named as 5,10-dideazafolic acid, as a microcrystalline colorless solid, mp>200° C.; NMR (TFA-d1) delta 2.3-2.7(m, 2H), 2.7-3.0(m, 2H), 3.25(s, 5H), 4.9-5.25(m, 1H), 7.35, 7.85(AB q, 4H, J=9 Hz), 8.50(s, 1H), 8.90(s, 1H).

Sources & evidence

ORD record
ord-b4c2191f57344380b397c36f7d982243
Source dataset
uspto-grants-1991_06
Patent number
US05026851

Reaction notes

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