Ammonia → Des-N-allyl cabergoline

HRID 2267081ノート

反応式

HRID 2267081 の反応式
[CH3:1][N:2]([CH3:44])[CH2:3][CH2:4][CH2:5][N:6]([C:39]([NH:41][CH2:42][CH3:43])=[O:40])[C:7]([C@@H:9]1[CH2:23][C@H:22]2[C@@H:12]([CH2:13][C:14]3[C:24]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]2=4)[N:16](C(OC(C)(C)C)=O)[CH:15]=3)[N:11](C(OC(C)(C)C)=O)[CH2:10]1)=[O:8].Cl.N>ClCCl>[CH3:44][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]([C:39]([NH:41][CH2:42][CH3:43])=[O:40])[C:7]([C@@H:9]1[CH2:23][C@H:22]2[C@@H:12]([CH2:13][C:14]3[C:24]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]2=4)[NH:16][CH:15]=3)[NH:11][CH2:10]1)=[O:8]

参加物

5

反応物 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 16050215HCID 16050215、化合物

生成物 1

HCID 9979008Des-N-allyl cabergoline収率 94.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
35 °C

実験手順

To 12.7 g (20.76 mmol) of N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl)-1,6-di(tert-butoxycarbonyl)-ergoline-8β-carboxamide (XVIII, R2=tert-butyl) 230 ml of 4M aqueous hydrochloric acid was added, and the reaction was stirred at 35° C. for 2 hours. The reaction mixture was cooled to ambient temperature, 200 ml of dichloromethane was added and the pH was adjusted to 11 with concentrated aqueous ammonia solution. The organic layer was separated and the aqueous layer was extracted with 2×60 ml of dichloromethane. The combined organic layer was dried over anhydrous sodium sulphate. The dried solution was either subjected to the subsequent step without isolation of the product or it was concentrated in vacuum to give 8.1 g (94.8%) of the title compound.

後処理

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 2×60 ml of dichloromethane
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  5. concentrationwas concentrated in vacuum

出典と根拠

ORDレコード
ord-f111a5272cb34221ba2cee46be8eab5b
出典データセット
uspto-grants-2010_12
特許番号
US07858791B2

反応ノート

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