Ethanol → HCID 135577946, compound

HRID 1638604Notes

Reaction equation

HRID 1638604 reaction equation
O.C([NH:5][C:6]1[NH:7][C:8](=[O:42])[C:9]([CH2:19][CH2:20][NH:21][C:22]2[CH:41]=[CH:40][C:25]([C:26]([NH:28][C@H:29]([C:36]([O:38]C)=[O:37])[CH2:30][CH2:31][C:32]([O:34]C)=[O:33])=[O:27])=[CH:24][CH:23]=2)=[C:10]([N:12](C(=O)C)C(=O)C)[N:11]=1)(=O)C.C(O)C.SCCO>[OH-].[Na+]>[NH2:5][C:6]1[NH:7][C:8](=[O:42])[C:9]([CH2:19][CH2:20][NH:21][C:22]2[CH:41]=[CH:40][C:25]([C:26]([NH:28][C@H:29]([C:36]([OH:38])=[O:37])[CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:27])=[CH:24][CH:23]=2)=[C:10]([NH2:12])[N:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 15672-MercaptoethanolHCID 136364562HCID 136364562, compound

Product 1

HCID 135577946HCID 135577946, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A crude preparation of dimethyl N-[4-[2-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)ethylamino]benzoyl]-L-glutamate hydrate (prepared on a 3.3 mmol scale but without recrystallization) was dissolved in 1N sodium hydroxide (100 ml) and ethanol (50 ml) containing 2-mercaptoethanol (0.25 ml). The reaction was heated with stirring to 55° for 18 hours and then spin evaporated in vacuo to a small volume. The pH of the ice bath cooled solution was adjusted to pH 4 with hydrochloric acid (12 N) to precipiate the product. Recrystallization from methanol/ether gave 0.52 g (38% of theory) of N-[4-[2-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)ethylamino]benzoyl]-L-glutamic acid, mp 180°-185°.

Workup

  1. customprepared on a 3.3 mmol scale but without recrystallization)
  2. temperatureThe reaction was heated
  3. customspin evaporated in vacuo to a small volume
  4. temperatureThe pH of the ice bath cooled solution
  5. customRecrystallization from methanol/ether

Sources & evidence

ORD record
ord-90a03abcbb33489895bae764aebf38df
Source dataset
uspto-grants-1989_11
Patent number
US04880812

Reaction notes

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