HCID 178471568, compound → HCID 178439179, compound

HRID 1494620Notes

Reaction equation

HRID 1494620 reaction equation
C([NH:4][C:5]1[N:6]=[C:7]([OH:40])[C:8]2[CH2:14][CH:13]([CH:15]([CH3:39])[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)[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]([CH:15]([CH3:39])[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)[CH2:12][NH:11][C:9]=2[N:10]=1

Participants

3

Reactant 1

HCID 178471568HCID 178471568, compound

Product 1

HCID 178439179HCID 178439179, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A homogeneous solution of 17.5 mg of diethyl N-(4-[2-(2-acetamido-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)propyl]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-5f3149737104482387ca37d0e6726843
Source dataset
uspto-grants-1991_06
Patent number
US05026851

Reaction notes

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