Water → HCID 659308, compound

HRID 2184646Notes

Reaction equation

HRID 2184646 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([C@@H:13]([C@H:15]([C:17]([O:19]CC)=O)[OH:16])[OH:14])([O:10]CC)=O.O>CO>[CH:1]1([NH:7][C:8](=[O:10])[C@@H:13]([C@H:15]([C:17]([NH:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:19])[OH:16])[OH:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 7965Cyclohexylamine2×HCID 6993580Diethyl tartrate3×

Product 1

HCID 659308HCID 659308, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

N,N′-Di-cyclohexyl L-tartaramide was prepared by the reaction of cyclohexyl amine with diethyl L-tartrate. Diethyl L-tartrate (19.997 g, 1.0 eq) and HPLC grade methanol (40 mL) were weighed into a 250 mL round-bottomed flask equipped with a teflon coated magnetic stir bar. Cyclohexyl amine (20.205 g, 2.0 eq) was slowly poured into the stirring diethyl L-tartrate solution. Some fuming and a color change from water-white to pale yellow were observed. Additional methanol (10 mL) was used to rinse all of the amine into the reaction flask. After stirring the solution for 30 min, the flask was stoppered and refrigerated at approximately 45° F. (70C). The product crystallized after 3 days at 45° F. (7° C.). The white crystals were filtered, washed with methanol (2×15 mL), and dried under vacuum. A first crop of 3.952 g (12.65 mmole, 13% yield) were obtained in this manner, and a second crop of 16.063 g were obtained by removing the solvent under vacuum. Overall yield was 66%.

Workup

  1. customequipped with a teflon coated magnetic stir bar
  2. washto rinse all of the amine into the reaction flask
  3. customrefrigerated at approximately 45° F.
  4. customThe product crystallized after 3 days at 45° F. (7° C.)
  5. filtrationThe white crystals were filtered
  6. washwashed with methanol (2×15 mL)
  7. customdried under vacuum
  8. customA first crop of 3.952 g (12.65 mmole, 13% yield) were obtained in this manner
  9. customa second crop of 16.063 g were obtained
  10. customby removing the solvent under vacuum

Sources & evidence

ORD record
ord-0a0d3e1a4a214fe68ae037515fa64d63
Source dataset
uspto-grants-2002_06
Patent number
US06399543B1

Reaction notes

Loading…