Ethanol → N-(4-{[3-(6-Amino-4-hydroxy-2-imino-1,2-dihydropyrimidin-5-yl)propyl]amino}benzoyl)glutamic acid

HRID 1638599Notes

Reaction equation

HRID 1638599 reaction equation
C([NH:4][C:5]1[NH:6][C:7](=[O:39])[C:8]([CH2:15][CH2:16][CH2:17][NH:18][C:19]2[CH:38]=[CH:37][C:22]([C:23]([NH:25][C@H:26]([C:33]([O:35]C)=[O:34])[CH2:27][CH2:28][C:29]([O:31]C)=[O:30])=[O:24])=[CH:21][CH:20]=2)=[C:9]([NH:11]C(=O)C)[N:10]=1)(=O)C.C(O)C.[OH-].[Na+].N1C=CC=CC=1>O.C(O)CCC>[NH2:4][C:5]1[NH:6][C:7](=[O:39])[C:8]([CH2:15][CH2:16][CH2:17][NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([NH:25][C@H:26]([C:33]([OH:35])=[O:34])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:24])=[CH:37][CH:38]=2)=[C:9]([NH2:11])[N:10]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 14798Sodium HydroxideHCID 135990644HCID 135990644, compound

Product 1

HCID 135407589N-(4-{[3-(6-Amino-4-hydroxy-2-imino-1,2-dihydropyrimidin-5-yl)propyl]amino}benzoyl)glutamic acid

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of 1.60 g (2.89 mmol) of dimethyl N-[4-[3-(2,4-bis(acetamido)-1,6-dihydro-6-oxo-5-pyrimidinyl)propylamino]benzoyl]-L-glutamate, 50 ml of ethanol and 100 ml of 1 N sodium hydroxide was heated at 50°-60° for 20 hours. The cooled reaction was spin evaporated in vacuo to 50 ml, cooled, and neutralized to pH 5-6 with concentrated hydrochloric acid. The resultant white precipitate was collected, washed with water, diethylether and dried; yield, 0.86 g (66%) mp (sinter 170°) 198°-202° (eff). Recrystallization from methanol gave the analytical sample; yield, 0.33 g (39%), mp (forms hard foam 180°) 200° (eff); TLC (pyridine:BuOH:H2O/1:1:1); NMR (DMSO-D6)δ8.07 (d, 1H, ArCONH), 7.65 (d, 2H, ArH), 6.54 (d, 2H, ArH), 6.22 (br s, 1H, CH2NH), 5.94 (s, 2H, NH2), 5.75 (s, 2H, NH2), 4.34 (m, 1H, CHCO2H), 3.03 (m, 2H, CH2NHAr), 2.30 (m, 4H, pyrimidine-CH2 and CH2CO2H), 2.03 (m, 2H, CHCH2), 1.58 (m, 2H, CH2CH2CH2).

Workup

  1. customThe cooled reaction
  2. customevaporated in vacuo to 50 ml
  3. temperaturecooled
  4. customThe resultant white precipitate was collected
  5. washwashed with water, diethylether
  6. customdried
  7. customyield
  8. custom0.86 g (66%) mp (sinter 170°) 198°-202° (eff)
  9. customRecrystallization from methanol
  10. customgave the analytical sample
  11. customyield
  12. custom0.33 g (39%), mp (forms hard foam 180°) 200° (eff)

Sources & evidence

ORD record
ord-05004dda8a084946b8973bb297035f26
Source dataset
uspto-grants-1989_11
Patent number
US04880812

Reaction notes

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