2,3-Dihydroxybutanedioic Acid → HCID 131724461, compound

HRID 353332Notes

Reaction equation

HRID 353332 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:45])(=[O:44])[CH:37]([CH:39]([C:41]([OH:43])=[O:42])[OH:40])[OH:38]>C(OCC)(=O)C>[OH:40][C@H:39]([C@@H:37]([OH:38])[C:36]([OH:45])=[O:44])[C:41]([OH:43])=[O:42].[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 8752,3-Dihydroxybutanedioic AcidHCID 9892815HCID 9892815, compound

Product 1

HCID 131724461HCID 131724461, compoundYield 99.7%

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 tartaric acid (48 mg, 0.3 mmol) and solution was stirred at ambient temperature for 2 hours. Evaporation of the solvent and recrystallization from hot ethanol at zero degrees Celsius gave the title compound as a white solid (0.2 g, 58.3%). Analytical calculation for C22H25N2O7SF3.0.5C4H6O6.1.25H2O: C, 46.79; H, 4.99; N, 4.55; S, 5.20. Found: C, 47.17; H, 5.20; N, 4.07; S, 5.03

Workup

  1. customEvaporation of the solvent and recrystallization from hot ethanol at zero degrees Celsius

Sources & evidence

ORD record
ord-011e3724b1bd44018783a538dbd16082
Source dataset
uspto-grants-2004_06
Patent number
US06750228B1

Reaction notes

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