Methanol → tert-Butyl 2-(2-(6-(methylsulfonamido)-4-oxospiro[chroman-2,4'-piperidine]-1'-yl)ethoxy)ethylcarbamate

HRID 1093902노트

반응식

HRID 1093902 반응식
C(N(CC)C(C)C)(C)C.Br[CH2:11][CH2:12][O:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].Cl.[O:25]=[C:26]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])[CH:39]=2)[O:34][C:28]2([CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH2:27]1.CO>CN(C=O)C.ClCCl.C(OCC)(=O)C.O>[CH3:45][S:42]([NH:41][C:38]1[CH:39]=[C:40]2[C:35](=[CH:36][CH:37]=1)[O:34][C:28]1([CH2:29][CH2:30][N:31]([CH2:11][CH2:12][O:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:32][CH2:33]1)[CH2:27][C:26]2=[O:25])(=[O:43])=[O:44]

참가 물질

9

반응물 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 19045253N-(4-Oxospiro[chroman-2,4'-piperidine]-6-yl)methanesulfonamide hydrochloride2회HCID 22712752tert-butyl N-[2-(2-bromoethoxy)ethyl]carbamate

생성물 1

HCID 57903876tert-Butyl 2-(2-(6-(methylsulfonamido)-4-oxospiro[chroman-2,4'-piperidine]-1'-yl)ethoxy)ethylcarbamate수율 134.9%

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of N,N-diisopropylethylamine (1.3 mL, 7.5 mmol), tert-butyl 2-(2-bromoethoxy)ethyl-carbamate (4, 0.59 g, 2.2 mmol), and N-(4-oxospiro[chroman-2,4′-piperidine]-6-yl)methanesulfon-amide hydrochloride (11, 0.5 g, 1.4 mmol) in 10 mL of anhydrous DMF was stirred at 60-65° C. After ˜24 hours TLC (silica gel, 10% methanol in dichloromethane, UV visualization) showed almost complete disappearance of starting amine 11 (Rf=0.02−0.06) and appearance of one major new product (Rf=0.35-0.45). The reaction was allowed to cool to room temperature and 10 mL of water was added. The resulting mixture was transferred to a separatory funnel with the aid of ethyl acetate and the layers were separated. The aqueous layer was extracted with 20 mL of ethyl acetate. The organic extracts were combined, washed successively with 10 mL portions of water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure on a rotary evaporator followed by high vacuum to provide 0.94 g of orange-brown oil.

후처리

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with 20 mL of ethyl acetate
  3. washwashed successively with 10 mL portions of water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure on a rotary evaporator

출처 및 근거

ORD 기록
ord-0a3d688279de42bb9d46e412936e6f85
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133695B2

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