Hydrochloric Acid → HCID 178508896, compound

HRID 1108285Notes

Reaction equation

HRID 1108285 reaction equation
C([NH:7][C:8]1[N:9]=[C:10]([OH:41])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[S:21][CH:22]=[C:23]([C:25]([NH:27][C@H:28]([C:36]([O:38]CC)=[O:37])[CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])=[O:26])[N:24]=3)[CH2:15][NH:14][C:12]=2[N:13]=1)(=O)C(C)(C)C.Cl>[OH-].[Na+]>[NH2:7][C:8]1[N:9]=[C:10]([OH:41])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[S:21][CH:22]=[C:23]([C:25]([NH:27][C@H:28]([C:36]([OH:38])=[O:37])[CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:26])[N:24]=3)[CH2:15][NH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178471583HCID 178471583, compound

Product 1

HCID 178508896HCID 178508896, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a 25 mL 14/20 round bottom flask was charged 0.067 g (0.11 mmol) of diethyl N-{2-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]-4-thiazolylcarbonyl}-L-glutamate dissolved in 3 mL of 1N sodium hydroxide. The reaction was stirred at room temperature for 84 hours The solution was cooled down in an ice bath and acidified with 1N hydrochloric acid to pH 3. The precipitate was filtered, washed with 25 mL water, and dried in a vacuum oven at 60° C. to give 0.036 g (70%) of N-{2-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]-4-thiazolylcarbonyl}-L-glutamic acid m.p. 210-212° C. as a tan solid. Rf =0.08 (50% methanol/chloroform); 1H NMR (300 MHz, DMSO d6) δ 1.69-2.09 (m, 8H), 2.26 (t, J=7.1 Hz, 2H), 2.80 (t, J=8.2 Hz, 2H), 3.05-3.17 (m, 2H), 4.34-4.41 (m, 1H), 5.93 (s, 2H), 6.26 (s, 1H), 8.12 (s, 1H), 8.33 (d, J=7.7 Hz, 1H), 9.70 (br s, 1H).

Workup

  1. temperaturewas cooled down in an ice bath
  2. filtrationThe precipitate was filtered
  3. washwashed with 25 mL water
  4. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-183bb7dcfbf54f2da94e836ca4331187
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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