HCID 178471567, compound → HCID 178439557, compound

HRID 231304Notes

Reaction equation

HRID 231304 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-a4cf7bed5f4443ccab8bed2801e329e9
Source dataset
uspto-grants-1989_07
Patent number
US04845216

Reaction notes

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