Hydrochloric Acid → HCID 136207606, compound

HRID 2051566Notes

Reaction equation

HRID 2051566 reaction equation
C([NH:4][C:5]1[NH:6][C:7](=[O:46])[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[O:44][CH3:45])=[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:46])[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[O:44][CH3:45])=[C:9]([NH2:11])[N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136054893HCID 136054893, compound

Product 1

HCID 136207606HCID 136207606, 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-methoxybenzoyl]-(L)-glutamate (1.00 g, 1.55 mmoles) in 1.0N sodium hydroxide (25 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 6N hydrochloric acid. After stirring cold 0.5 hour, the resulting precipitate was filtered, rinsed with pH 2.1 aqueous hydrochloric acid (2×25 mL), and dried to give a white solid; yield, 596 mg (83%); mp 165°-184° C. (grad. dec.); 1H-NMR (DMSO-d6) δ 1.56 (m, 2H), 1.8-2.2 (br m, 2H), 2.2-2.4 (m, 4H), 3.07 (m, 2H), 3.81 (s, 3H), 4.37 (m, 1H), 5.6 (br s, 1H), 5.74 (s, 2 H), 5.93 (s, 2H), 6.49 (d, Jo =8 Hz, 1H), 7.29 (d, Jm =2 Hz, 1H), 7.41 (dxd, Jo =8 Hz, Jm =2 Hz, 1H), 8.15 (d, 1H), 9.8 (v br s, 1H), 12.3 (v br s, 2H); uv (0.1N NaOH) 306 nm max (15100), 287 min (11700), 273 max (15200), 250 min (6500), 215 max (25800). Anal. Calcd. for C20H26N6O7.0.7H2O (Mr 475.07): C, 50.56; H, 5.81; N, 17.69. Found: C, 50.58; H, 5.85; N, 17.63.

Workup

  1. temperatureThe reaction mixture was chilled (ice bath)
  2. filtrationthe resulting precipitate was filtered
  3. washrinsed with pH 2.1 aqueous hydrochloric acid (2×25 mL)
  4. customdried
  5. customto give a white solid
  6. customyield

Sources & evidence

ORD record
ord-265565e6382949f4a0aadd5fd3b4ec10
Source dataset
uspto-grants-1991_05
Patent number
US05019577

Reaction notes

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