Methane → HCID 178508900, compound

HRID 2350909Notes

Reaction equation

HRID 2350909 reaction equation
C([NH:7][C:8]1[N:9]=[C:10]([OH:49])[C:11]2[CH2:17][CH:16]([CH2:18][N:19]([CH2:26][C:27]3[CH:48]=[CH:47][C:30]([C:31]([NH:33][C@H:34]([C:42]([O:44]CC)=[O:43])[CH2:35][CH2:36][C:37]([O:39]CC)=[O:38])=[O:32])=[CH:29][CH:28]=3)C(=O)C(F)(F)F)[CH2:15][NH:14][C:12]=2[N:13]=1)(=O)C(C)(C)C.C>[OH-].[Na+]>[NH2:7][C:8]1[N:9]=[C:10]([OH:49])[C:11]2[CH2:17][CH:16]([CH2:18][NH:19][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([C:31]([NH:33][C@H:34]([C:42]([OH:44])=[O:43])[CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[O:32])=[CH:47][CH:48]=3)[CH2:15][NH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 297MethaneHCID 178471578HCID 178471578, compound

Product 1

HCID 178508900HCID 178508900, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.48 g, of diethyl N-[N-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]-pyrimidin-6-ylmethyl)-N-trifluoroacetyl-4-aminomethylbenzoyl]-glutamate in 10 mL of 1N sodium hydroxide was stirred at 25° C. for 72 hours. To the reaction mixture was added charcoal and the suspension filtered through Celite. The filtrate was rendered acidic with acetic acid and stored at 0° C. for 4 hours. The solid which formed was collected, and washed sequentially with water, ethanol, and ether to give 0.241 g (76% yield) of N-[N-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-ylmethyl)-4-aminomethylbenzoyl]-glutamic acid; mp 263° C. (dec); 1H NMR (Me2SO d6) delta 1.8-2.25 (m, 4H), 2.27 (t, 2H, J=6.95 Hz), 2.73-3.00 (m, 2H), 3.28-3.31 (m, 1H), 4.05 (s, 2H), 4.14 (s, 2H), 4.21 (s, 2H), 4.36-4.41 (m, 1H), 7.41-7.7.45 (m, 2H, AA'BB'), 7.80-7.82 (m, 2H, AA'BB'), 8.61 (s, 1H). Anal. Calcd for C21H26N6O6.H2O: C, 53.95; H, 5.82; N, 17.97. Found: C, 54.07; H, 5.48; N, 17.76.

Workup

  1. filtrationthe suspension filtered through Celite
  2. customThe solid which formed
  3. customwas collected
  4. washwashed sequentially with water, ethanol, and ether

Sources & evidence

ORD record
ord-f2a509c620684054ba9a15c681a6979c
Source dataset
uspto-grants-1989_10
Patent number
US04871746

Reaction notes

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