Sodium Hydroxide → 7-({2-[benzyl(methyl)amino]ethoxy}methyl)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

HRID 1669493ノート

反応式

HRID 1669493 の反応式
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:28]([O:30]C)=[O:29])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([CH2:26][OH:27])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[Cl-].[CH2:35]([NH+:42]([CH3:46])[CH2:43][CH2:44]Cl)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:35]([N:42]([CH3:46])[CH2:43][CH2:44][O:27][CH2:26][CH:16]1[CH2:15][N:14]2[C:13]3[CH:12]=[C:11]([C:28]([OH:30])=[O:29])[CH:10]=[CH:9][C:8]=3[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:21]2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 31967Benzylamine, N-(2-chloroethyl)-N-methyl-, hydrochlorideHCID 66674539HCID 66674539、化合物

生成物 1

HCID 866279097-({2-[benzyl(methyl)amino]ethoxy}methyl)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒

反応条件

温度
65 °C

実験手順

A solution of (+)-methyl 14-cyclohexyl-7-(hydroxymethyl)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (second eluting isomer) in toluene (0.04 M) was treated with 30% w/v NaOH (10 eq) and tetrabutylammonium bromide (0.25 eq) followed by N-benzyl-2-chloro-N-methylethanaminium chloride (prepared as described in example 7 step 1) (2.5 eq). The resulting solution was stirred at 65° C. for 18 h. Toluene was removed in vacuo, the residue was taken up in EtOAc and washed with 1N HCl (aq) and brine before drying (Na2SO4), filtering and concentrating in vacuo to afford the product as an oil that was used without further purification. (ES+) m/z 553 (M+H)+.

後処理

  1. customToluene was removed in vacuo
  2. washwashed with 1N HCl (aq) and brine
  3. dry with materialbefore drying (Na2SO4)
  4. filtrationfiltering
  5. concentrationconcentrating in vacuo

出典と根拠

ORDレコード
ord-98a6c263c3fd43759dce62a44175fd1d
出典データセット
uspto-grants-2011_08
特許番号
US07989438B2

反応ノート

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