Citric Acid → HCID 22707824, compound

HRID 353331Notes

Reaction equation

HRID 353331 reaction equation
[OH:1][NH:2][C:3]([C:5]1([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][O:13][CH3:14])[CH2:7][CH2:6]1)=[O:4].[C:36]([OH:48])(=[O:47])[CH2:37][C:38]([CH2:43][C:44]([OH:46])=[O:45])([C:40]([OH:42])=[O:41])[OH:39]>C(OCC)(=O)C>[OH:39][C:38]([C:40]([OH:42])=[O:41])([CH2:43][C:44]([OH:46])=[O:45])[CH2:37][C:36]([OH:48])=[O:47].[OH:1][NH:2][C:3]([C:5]1([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][C:32]([F:35])([F:33])[F:34])=[CH:29][CH:30]=3)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][O:13][CH3:14])[CH2:9][CH2:10]1)=[O:4]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 9892815HCID 9892815, compound

Product 1

HCID 22707824HCID 22707824, compoundYield 121.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Part A: To a solution of Example 252 (0.3 g, 0.578 mmol) in ethyl acetate (5 mL) was added citric acid (41 mg, 0.21 mmol) and the solution was stirred at ambient temperature for 2 hours. Evaporation of the solvent and recrystallization from hot ethanol gave the title compound as a white crystalline solid (0.181 g, 53.7%). Analytical calculation for C22H25N2O7SF3.(1/3)C6H9O7.0.9H2O: C, 48.34; H, 4.99; N, 4.70; S, 5.38. Found: C, 48.42; H, 4.99; N, 4.70; S, 5.38.

Workup

  1. customEvaporation of the solvent and recrystallization from hot ethanol

Sources & evidence

ORD record
ord-3b8ee11c1efa446ea924c93603f3cf01
Source dataset
uspto-grants-2004_06
Patent number
US06750228B1

Reaction notes

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