HCID 178471567, compound → HCID 178439557, compound

HRID 1788718Notes

Reaction equation

HRID 1788718 reaction equation
C([NH:4][C:5]1[N:6]=[C:7]([OH:40])[C:8]2[CH2:14][CH:13]([CH2:15][CH:16]([C:18]3[CH:39]=[CH:38][C:21]([C:22]([NH:24][C@H:25]([C:33]([O:35]CC)=[O:34])[CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[O:23])=[CH:20][CH:19]=3)[CH3:17])[CH2:12][NH:11][C:9]=2[N:10]=1)(=O)C>[OH-].[Na+]>[NH2:4][C:5]1[N:6]=[C:7]([OH:40])[C:8]2[CH2:14][CH:13]([CH2:15][CH:16]([C:18]3[CH:19]=[CH:20][C:21]([C:22]([NH:24][C@H:25]([C:33]([OH:35])=[O:34])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:23])=[CH:38][CH:39]=3)[CH3:17])[CH2:12][NH:11][C:9]=2[N:10]=1

Participants

3

Reactant 1

HCID 178471567HCID 178471567, compound

Product 1

HCID 178439557HCID 178439557, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A homogeneous solution of 17.5 mg of diethyl N-(4-[1-(2-acetamido-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)prop-2-yl]benzoyl)-L-glutamate in 2 mL of methanolic sodium hydroxide solution was allowed to stand at room temperature for 72 hours. Most of the solvent was then removed under reduced pressure and the mixture was diluted with water and acidified with acetic acid. The precipitate was collected by filtration, washed with water, and dried under reduced pressure (0.1 mm) for 48 hours to give 9.7 mg (67%) of the title compound, which may be alternatively named as 5,10-dideaza-10-methyl-5,6,7,8-tetrahydrofolic acid. mp >250° C., NMR delta 0.87-0.88 (brs, 1H each), 1-2.8 (m, 11H), 3.13 (m, 1H), 4.59 (m, 1H), 6.96 (d, 2H, J=9 Hz), 7.34 (d, 2H, J=9 Hz.

Workup

  1. customMost of the solvent was then removed under reduced pressure
  2. additionthe mixture was diluted with water
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure (0.1 mm) for 48 hours

Sources & evidence

ORD record
ord-5235adf5a47c4d5ea3963a1686188611
Source dataset
uspto-grants-1987_08
Patent number
US04684653

Reaction notes

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