Acetic Acid → HCID 178508893, compound

HRID 1108273Notes

Reaction equation

HRID 1108273 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([OH:33])[C:5]2[CH2:11][CH:10]([CH2:12][CH2:13][C:14]3[CH:15]=[C:16]([C:19]([NH:21][C@H:22]([C:29]([O:31]C)=[O:30])[CH2:23][CH2:24][C:25]([O:27]C)=[O:26])=[O:20])[NH:17][CH:18]=3)[CH2:9][NH:8][C:6]=2[N:7]=1.C(O)(=O)C>[OH-].[Na+]>[NH2:1][C:2]1[N:3]=[C:4]([OH:33])[C:5]2[CH2:11][CH:10]([CH2:12][CH2:13][C:14]3[CH:15]=[C:16]([C:19]([NH:21][C@H:22]([C:29]([OH:31])=[O:30])[CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:20])[NH:17][CH:18]=3)[CH2:9][NH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 178500477HCID 178500477, compound

Product 1

HCID 178508893HCID 178508893, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of dimethyl N-{4-[2-(amino-4-hydroxy-5,6,7,8-tetrahydropyrido-[2,3-d]pyrimidin-6-yl)ethyl]pyrrol-2-ylcarbonyl}-L-glutamate (92 mg, 0.2 mmol) in 1N sodium hydroxide (1 mL) was stirred at room temperature for 3 days, then acidified to pH 5 by addition of glacial acetic acid. The white solid was collected by filtration, washed with water, and dried in vacuo to give N-{4-[2-(amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]pyrrol-2-ylcarbonyl}-L-glutamic acid (68 mg, 79%) as a white solid: 1H NMR (DMSO-d6) δ 11.44 (s, 1H), 9.84 (br s, 1H), 7.79 (d, 1H, J=7.7 Hz), 6.64 (s, 2H), 6.23 (s, 1H), 5.97 (s, 2H), 4.27 (s, 1H), 3.16 (brd, 1H, J=9.6 Hz), 2.74 (brt, 1H, J=10.2 Hz), 2.45-2.18 (m, 5H), 1.95-1.75 (m, 3H), 1.65-1.40 (m, 3H). HR FAB MS calcd for C19H25N6O6 433.1836 (M+ +H), found 433.1866.

Workup

  1. filtrationThe white solid was collected by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-160a9f204a1c4113ad60271a69d21d7f
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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