Citric Acid → HCID 136481381, compound

HRID 2085994Notes

Reaction equation

HRID 2085994 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)[N:5]=[C:6]2[C:11](=[O:12])[NH:10][C:9]([C:13]3[CH:18]=[C:17]([S:19]([N:22]4[CH2:27][CH2:26][N:25]([CH2:28][CH3:29])[CH2:24][CH2:23]4)(=[O:21])=[O:20])[CH:16]=[CH:15][C:14]=3[O:30][CH2:31][CH2:32][CH3:33])=[N:8][C:7]=12)[CH3:2].[C:41]([OH:53])(=[O:52])[CH2:42][C:43]([CH2:48][C:49]([OH:51])=[O:50])([C:45]([OH:47])=[O:46])[OH:44]>CC(C)=O.O>[C:41]([OH:53])(=[O:52])[CH2:42][C:43]([CH2:48][C:49]([OH:51])=[O:50])([C:45]([OH:47])=[O:46])[OH:44].[CH2:1]([C:3]1[N:4]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)[N:5]=[C:6]2[C:11](=[O:12])[NH:10][C:9]([C:13]3[CH:18]=[C:17]([S:19]([N:22]4[CH2:27][CH2:26][N:25]([CH2:28][CH3:29])[CH2:24][CH2:23]4)(=[O:21])=[O:20])[CH:16]=[CH:15][C:14]=3[O:30][CH2:31][CH2:32][CH3:33])=[N:8][C:7]=12)[CH3:2]

Participants

5

Reactant 2

HCID 311Citric AcidHCID 135430996UK-343664

Product 1

HCID 136481381HCID 136481381, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

A stirred mixture of the title compound of Example 5A (15.0 g, 26.5 mmol) and acetone (150 ml) was heated under reflux, then filtered. To the stirred filtrate was added a filtered solution of citric acid (5.10 g, 26.5 mmol) in a mixture of acetone (75 ml) and water (7.5 ml), then the reaction mixture heated under reflux for 75 minutes and allowed to cool. The resulting suspension was granulated for 1 hour and filtered, then the solid thus obtained washed with acetone (20 ml) and dried at 45° C. to provide the title compound (18.33 g, 91%) as a white solid, m.p. 185° C. Found: C, 53.84; H, 5.71; N, 12.89. C28H35N7O4S; C6H8O7 requires C, 53.89; H, 5.72; N, 12.94. δ (DMSOd6): 0.95 (6H, m), 1.20 (3H, t), 1.72 (2H, m), 2.40-2.73 (10H, m), 2.96 (4H, m), 4.11 (2H, t), 5.68 (2H, s), 7.21 (1H, d), 7.34 (2H, m), 7.82 (3H, m), 8.51 (1H, d), 11.72 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. filtrationfiltered
  4. temperaturethe reaction mixture heated
  5. temperatureunder reflux for 75 minutes
  6. temperatureto cool
  7. filtrationfiltered
  8. customthe solid thus obtained
  9. washwashed with acetone (20 ml)
  10. customdried at 45° C.

Sources & evidence

ORD record
ord-f9ccc5a360824636815505b920eec440
Source dataset
uspto-grants-2004_04
Patent number
US06723719B1

Reaction notes

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