Lauric Acid → Codeine laurate

HRID 1383792

反応式

HRID 1383792 の反応式
[CH3:1][N:2]1[C@@H:7]2[CH2:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]4[O:17][C@H:18]5[C@@H:19]([OH:22])[CH:20]=[CH:21][C@@H:6]2[C@:5]5([C:10]=34)[CH2:4][CH2:3]1.[C:23]([OH:36])(=[O:35])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>C(O)C.C(O)C.CN1[C@@H]2CC3C=CC(OC)=C4O[C@H]5[C@@H](O)C=C[C@@H]2[C@]5(C=34)CC1.C(OCC)(=O)C>[CH3:1][N:2]1[C@@H:7]2[CH2:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]4[O:17][C@H:18]5[C@@H:19]([OH:22])[CH:20]=[CH:21][C@@H:6]2[C@:5]5([C:10]=34)[CH2:4][CH2:3]1.[C:23]([O-:36])(=[O:35])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

参加物

6

反応物 2

HCID 3893Lauric AcidHCID 5284371Codeine

生成物 1

HCID 86757113Codeine laurate収率 39.4%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒HCID 86757114Ethanol codeine溶媒

反応条件

温度
60 °C

実験手順

Codeine base (4.0002 g; 12.60 mmol) was dissolved in ethanol (100 mL; 99.7-100%) with stirring. Lauric acid (2.7822 g; 13.86 mmol; 10% excess relative to codeine base) was dissolved in the ethanol/codeine solution. The resulting solution was stirred for 5 minutes. The ethanol was removed by rotary-evaporation to give a pale yellow residue. The residue was redispersed in ethyl acetate (10 mL) by heating on a water bath (60° C.). Once all the material had redissolved the solution was placed at 4° C. for 16 hours. A white precipitate formed which was isolated by vacuum filtration. The precipitate was dried further in a vacuum oven for 16 hours at 40° C. to give codeine laurate (2.4757 g; 36.50%). The material was analysed by Differential Scanning Calorimetry in order to determine the melting point. However, thermal analysis from 50 to 200° C. showed no thermal event.

後処理

  1. stirringThe resulting solution was stirred for 5 minutes
  2. customThe ethanol was removed by rotary-evaporation
  3. customto give a pale yellow residue
  4. dissolutionOnce all the material had redissolved the solution
  5. customA white precipitate formed which
  6. customwas isolated by vacuum filtration
  7. customThe precipitate was dried further in a vacuum oven for 16 hours at 40° C.

出典と根拠

ORDレコード
ord-4130d9465716482f883cbae9ef2b03b5
出典データセット
uspto-grants-2001_07
特許番号
US06255502B1

関連ノート

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