Citric Acid → HCID 86605097, compound

HRID 1095402Notes

Reaction equation

HRID 1095402 reaction equation
[OH-].[K+].C1([C:9]([NH:11][CH:12]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:13]([OH:18])[C:14]([NH:16][NH2:17])=[O:15])=[O:10])CCCCC1.[C:25](=[S:27])=S.[C:28](O)(=O)[CH2:29][C:30]([CH2:35][C:36](O)=O)(C(O)=O)O.[CH3:41]O>>[OH:18][CH:13]([CH:14]1[O:15][C:25](=[S:27])[N:17]=[N:16]1)[C:12]([N:11]=[C:9]=[O:10])([CH:28]1[CH2:29][CH2:30][CH2:35][CH2:36][CH2:41]1)[CH:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1

Participants

6

Reactant 5

HCID 311Citric AcidHCID 887Methanol2×HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 59165007HCID 59165007, compound

Product 1

HCID 86605097HCID 86605097, compound

Procedure

To a solution of potassium hydroxide in methanol (1.0 M, 8.0 ml) was suspended 3-cyclohexylcarbonylamino-3-(tetrahydropyran-4-yl)-2-hydroxypropanohydrazide (prepared in step 5 in example 1; 2.0 g) and thereto were added methanol (16 ml) and carbon disulfide (0.46 ml) and the mixture was stirred for 3 hours at room temperature and followed by refluxing for 24 hours. The reaction mixture was poured into iced aqueous solution of citric acid and extracted with ethyl acetate. The organic layer was washed by water and brine successively, dried over magnesium sulfate and concentrated to give 5-(1-hydroxy-2-cyclohexyl carbonylamino-2-tetrahydropyran-4-ylethyl)-2-thioxo-1,3,4-oxadiazoline (2.41 g).

Workup

  1. temperatureby refluxing for 24 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed by water and brine successively
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a668ac3c54f1478496ee8638dd59b467
Source dataset
uspto-grants-2012_03
Patent number
US08138182B2

Reaction notes

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