Sodium hydride → HCID 67061784, 화합물

HRID 910801노트

반응식

HRID 910801 반응식
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

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 56924404(2R)-3-Methoxy-2-methylpropan-1-olHCID 67061878HCID 67061878, 화합물

생성물 1

HCID 67061784HCID 67061784, 화합물

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-148c59c4412a476eae5d580d264cff43
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022068B2

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