Triethylamine → N1-(2,2-dimethoxyethyl)-N2-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)oxalamide

HRID 562598노트

반응식

HRID 562598 반응식
Cl[C:2](=[O:8])[C:3](OCC)=[O:4].[NH2:9][C:10]1[CH:21]=[CH:20][C:13]([O:14][CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])=[C:12]([CH3:22])[CH:11]=1.CCN(CC)CC.[CH3:30][O:31][CH:32]([O:35][CH3:36])[CH2:33][NH2:34]>C1COCC1.CCOC(C)=O>[CH3:30][O:31][CH:32]([O:35][CH3:36])[CH2:33][NH:34][C:2](=[O:8])[C:3]([NH:9][C:10]1[CH:21]=[CH:20][C:13]([O:14][CH2:15][C:16]([OH:18])([CH3:19])[CH3:17])=[C:12]([CH3:22])[CH:11]=1)=[O:4]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 575405781-(4-Amino-2-methylphenoxy)-2-methylpropan-2-ol

생성물 1

HCID 57540557N1-(2,2-dimethoxyethyl)-N2-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)oxalamide수율 98.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

Slow addition of a solution of ethyl 2-chloro-2-oxoacetate (4.69 g, 34.4 mmol) in THF (30 ml) to a solution of 1-(4-amino-2-methylphenoxy)-2-methylpropan-2-ol (6.10 g, 31.2 mmol) in THF (100 mL) resulted in formation of a precipitate as the reaction stirred at RT for 30 min. At which time a solution of Et3N (13.06 mL, 94 mmol) and 2,2-dimethoxyethanamine (3.94 g, 37.5 mmol) in EtOAc (100 mL) was added prior to heating the mixture at reflux for 25 hours. After cooling and concentration under vacuum, the residue, following dilution with CH2Cl2, was extracted with aqueous 0.5 N HCl (2×150 ml). The CH2Cl2 layer was dried over sodium sulfate and concentrated to yield N1-(2,2-dimethoxyethyl)-N2-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)-oxalamide (11.40 g, 30.6 mmol, 98% yield) as white solid which was carried forward without further purification.

후처리

  1. customresulted in formation of a precipitate as the reaction
  2. temperatureto heating the mixture
  3. temperatureat reflux for 25 hours
  4. temperatureAfter cooling
  5. concentrationconcentration under vacuum
  6. extractionwas extracted with aqueous 0.5 N HCl (2×150 ml)
  7. dry with materialThe CH2Cl2 layer was dried over sodium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c67101f3eb6f456691cd353d4fdab6d4
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067420B2

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