Sodium hydride → HCID 67061784、化合物

HRID 910801ノート

反応式

HRID 910801 の反応式
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][C@@H:13]([CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[NH:12][CH2:11][C@@H:10]2[O:27][CH:28]([C:39]2[CH:40]=[CH:41][C:42]3[O:47][CH2:46][CH2:45][N:44]([CH2:48][CH2:49][CH2:50][O:51][CH3:52])[C:43]=3[CH:53]=2)[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:5][CH:4]=1.[CH3:54][O:55][CH2:56][C@H:57]([CH3:60])[CH2:58][OH:59].[H-].[Na+]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CN(C=O)C.O>[CH3:54][O:55][CH2:56][C@H:57]([CH3:60])[CH2:58][O:59][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][C@@H:13]([CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[NH:12][CH2:11][C@@H:10]2[O:27][CH:28]([C:39]2[CH:40]=[CH:41][C:42]3[O:47][CH2:46][CH2:45][N:44]([CH2:48][CH2:49][CH2:50][O:51][CH3:52])[C:43]=3[CH:53]=2)[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:5][CH:4]=1

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 56924404(2R)-3-Methoxy-2-methylpropan-1-olHCID 67061878HCID 67061878、化合物

生成物 1

HCID 67061784HCID 67061784、化合物

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1.0 mmol of 6-[(3R,4R,6S)-4-(4-chloromethyl-phenyl)-1-(toluene-4-sulfonyl)-6-triisopropylsilanyloxymethyl-piperidin-3-yloxymethyl]-4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazine, 1.5 mmol of (R)-3-methoxy-2-methyl-propan-1-ol [911855-78-2] and 0.1 mmol of TBAI in 5 ml of DMF are added 1.65 mmol of NaH (55% in dispersion oil) at 0° C. The reaction mixture is allowed to warm to RT and stirred overnight, diluted with water, extracted with TBME and the organic phase is dried over Na2SO4. The organic phase is concentrated under reduced pressure and the residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a pale yellow oil. Rf=0.20 (EtOAc/heptane 1:2).

後処理

  1. extractionextracted with TBME
  2. dry with materialthe organic phase is dried over Na2SO4
  3. concentrationThe organic phase is concentrated under reduced pressure
  4. customthe residue is purified by flash chromatography (SiO2 60 F)

出典と根拠

ORDレコード
ord-148c59c4412a476eae5d580d264cff43
出典データセット
uspto-grants-2011_09
特許番号
US08022068B2

反応ノート

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