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

HRID 1094475노트

반응식

HRID 1094475 반응식
[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]

참가 물질

7

반응물 3

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

생성물 2

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1ccb86fc64b94d81ae056aaeecf7bd78
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133915B2

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