Methanol → HCID 178508886, compound

HRID 330369Notes

Reaction equation

HRID 330369 reaction equation
C([NH:7][C:8]1[N:9]=[C:10]([OH:42])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[CH:41]=[CH:40][C:23]([C:24]([NH:26][C@H:27]([C:35]([O:37]CC)=[O:36])[CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[O:25])=[CH:22][CH:21]=3)[CH2:15][NH:14][C:12]=2[N:13]=1)(=O)C(C)(C)C.[OH-].[Na+].CO>C(O)(=O)C>[NH2:7][C:8]1[N:9]=[C:10]([OH:42])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([C:24]([NH:26][C@H:27]([C:35]([OH:37])=[O:36])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:25])=[CH:40][CH:41]=3)[CH2:15][NH:14][C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 178471559HCID 178471559, compound

Product 1

HCID 178508886HCID 178508886, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.53 g of diethyl N-(4-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]-pyrimidin-6-yl)ethyl]benzoyl)-L-glutamate, 3 mL of 1N sodium hydroxide, and 50 mL of methanol is stirred at room temperature for 70 hours and then acidified with glacial acetic acid and filtered. The solid thus collected is washed with methanol and dried to yield N-(4-[2-(2-amino-4-hydroxy-5,6,7,8tetrahydropyrido-[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-L-glutamic acid, m.p. >250° C.; 1NMR (dTFA) delta 7.85 (d, J=7.9 Hz, 2H, Ar), 7.45 (d, J=9 Hz, 2H, Ar), 5.00-5.25 (m, 1H, CH2COOH), 1.7-3.9 (m, 13H, CH, 2° aliphatic).

Workup

  1. filtrationfiltered
  2. customThe solid thus collected
  3. washis washed with methanol
  4. customdried

Sources & evidence

ORD record
ord-fc196011f8134823a0d85893fed70c42
Source dataset
uspto-grants-1990_01
Patent number
US04895946

Reaction notes

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