Sodium hydride → HCID 68681230, 화합물

HRID 2353947노트

반응식

HRID 2353947 반응식
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([CH3:11])[C:5]=1[NH:12][C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14].[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([CH3:11])[C:5]=1[N:12]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:13]([O:15][CH:16]([CH3:17])[CH3:18])=[O:14]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 686790502-Isopropoxycarbonylamino-4-bromo-3-methyl-benzoic acid methyl ester

생성물 1

HCID 68681230HCID 68681230, 화합물수율 77%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

Add a solution of 2-Isopropoxycarbonylamino-4-bromo-3-methyl-benzoic acid methyl ester (3.36 g, 10.18 mmol) in DMF (37 mL) to a suspension of sodium hydride 60% dispersion mineral oil (407 mg, 10.18 mmol) in DMF (37 mL) at 0° C. under an atmosphere of nitrogen and allow to reach room temperature over 1 h. Add ethyl 4-bromobutyrate (2.2 mL, 15.27 mmol) and stir at room temperature for 14 h. Dilute with ethyl acetate, wash with 1M HCl, water and brine. Dry the organic layer over anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to provide the titled compound (3.47 g, 77%): MS (ES+): 445 (M+H).

후처리

  1. washwash with 1M HCl, water and brine
  2. dry with materialDry the organic layer over anhydrous magnesium sulfate
  3. filtrationfilter
  4. customremove the solvent under reduced pressure
  5. customPurify the residue by flash chromatography
  6. washeluting with hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-e61dec3c8eb94bf4b000dd9bbd1d7d35
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07749992B2

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