Methanol → HCID 178508886, compound

HRID 2259447Notes

Reaction equation

HRID 2259447 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-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-L-glutamic acid, m.p. >250° C.; 1H NMR (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-c68b875bbe534f2da6b05e0d89a31de8
Source dataset
uspto-grants-1995_12
Patent number
US05473071

Reaction notes

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