Hydrochloric Acid → HCID 136107974, compound

HRID 2051562Notes

Reaction equation

HRID 2051562 reaction equation
C([NH:4][C:5]1[NH:6][C:7](=[O:45])[C:8]([CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:43]=[CH:42][C:25]([C:26]([NH:28][C@H:29]([C:37]([O:39]CC)=[O:38])[CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[O:27])=[CH:24][C:23]=2[CH3:44])=[C:9]([N:11](C(=O)C)C(=O)C)[N:10]=1)(=O)C.Cl>[OH-].[Na+]>[NH2:4][C:5]1[NH:6][C:7](=[O:45])[C:8]([CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:43]=[CH:42][C:25]([C:26]([NH:28][C@H:29]([C:37]([OH:39])=[O:38])[CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:27])=[CH:24][C:23]=2[CH3:44])=[C:9]([NH2:11])[N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136023090HCID 136023090, compound

Product 1

HCID 136107974HCID 136107974, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

A solution of diethyl N-[4-(3-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propylamino)-3-methylbenzoyl]-(L)-glutamate (0.70 g, 1.1 mmoles) in 1.0N sodium hydroxide (20 mL) was stirred at 55° C. under nitrogen for 18 hours. The reaction mixture was chilled (ice bath) and adjusted to pH 2.5 by the gradual dropwise addition of 6.0N hydrochloric acid. After stirring cold 2 hours, the resulting precipitate was filtered. An attempted recrystallization of the wet cake from dimethylformamide/water failed, so the solution was spin evaporated to a clear oil. The oil was mixed with pH 2.1 aqueous HCl (20 mL) and sonicated 5 minutes to obtain a cream solid which was filtered and dried to give the product; yield, 0.12 g (24%); mp 181° C. (eff.); 1H-NMR (DMSO-d6) δ 1.58 (m, 2H), 1.8-2.1 (m, 2H), 2.12 (s, 3H), 2.2-2.4 (m, 4H), 3.08 (m, 2H), 4.34 (m, 1H), 5.78 (br s, 2H), 5.94 (br s, 2H), 6.52 (d, Jo=9 Hz, 1H), 7.53 (s overlapped, 1H), 7.57 (d overlapped, Jo=10 Hz, 1H), 8.06 (d, 1H), 10.0 (v br s, 1H), 12.2 (v br s, 2H); uv (0.1N NaOH) 296 nm max (18000), 286 min (17500), 274 max (19900), 247 min (5890), 215 max (21000).

Workup

  1. temperatureThe reaction mixture was chilled (ice bath)
  2. filtrationthe resulting precipitate was filtered
  3. customAn attempted recrystallization of the wet cake from dimethylformamide/water
  4. customevaporated to a clear oil
  5. additionThe oil was mixed with pH 2.1 aqueous HCl (20 mL)
  6. customsonicated 5 minutes
  7. customto obtain a cream solid which
  8. filtrationwas filtered
  9. customdried
  10. customto give the product
  11. customyield

Sources & evidence

ORD record
ord-44011bbefbb243c0896d350de16e4272
Source dataset
uspto-grants-1991_05
Patent number
US05019577

Reaction notes

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