Cyclohexylamine → ent-Kaur-16-en-19-oic acid

HRID 1367791Notes

Reaction equation

HRID 1367791 reaction equation
[CH3:1][C@:2]12[C@@H:11]3[CH2:12][CH2:13][C@@H:14]4[C:16]([CH2:18][C@@:10]3([CH2:15]4)[CH2:9][CH2:8][C@@H:7]1[C@@:6]([C:20]([OH:22])=[O:21])([CH3:19])[CH2:5][CH2:4][CH2:3]2)=[CH2:17].C(Cl)(C(Cl)=O)=O.[CH:29]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl.CN(C=O)C>[CH:29]1([NH-:35])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.[CH3:1][C@:2]12[C@@H:11]3[CH2:12][CH2:13][C@@H:14]4[C:16]([CH2:18][C@@:10]3([CH2:15]4)[CH2:9][CH2:8][C@@H:7]1[C@@:6]([C:20]([OH:22])=[O:21])([CH3:19])[CH2:5][CH2:4][CH2:3]2)=[CH2:17]

Participants

7

Reactant 3

HCID 7965CyclohexylamineHCID 65578Oxalyl chlorideHCID 3034087ent-Kaur-16-en-19-oic acid

Product 2

HCID 3034087ent-Kaur-16-en-19-oic acidHCID 19097440HCID 19097440, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Kaurenoic acid can be dissolved in dry CH2Cl2 and treated with 10 equivalents of (COCl)2 followed by two drops of DMF. When the reaction stops bubbling, the CH2Cl2 solvent and (COCl)2 can be evaporated under vacuum and the reaction residue can be redissolved in dry benzene and then treated with 5 equivalents of cyclohexylamine to yield N-cyclohexylamide derivative of kaurenoic acid.

Workup

  1. customWhen the reaction stops bubbling
  2. customthe CH2Cl2 solvent and (COCl)2 can be evaporated under vacuum
  3. dissolutionthe reaction residue can be redissolved in dry benzene

Sources & evidence

ORD record
ord-50fcb77e5d08421e9d08aac15ec2e905
Source dataset
uspto-grants-2011_02
Patent number
US07893299B2

Reaction notes

Loading…