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Triethylamine → N-methoxy-N-methyl-2-(1-phenylcyclobutyl)acetamide

HRID 1749157
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HRID 1749157 반응식
[C:1]1([C:7]2([CH2:11][C:12]([OH:14])=O)[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:16][NH:17][O:18][CH3:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl.O>[CH3:19][O:18][N:17]([CH3:16])[C:12](=[O:14])[CH2:11][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:10][CH2:9][CH2:8]1
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534291062-(1-Phenylcyclobutyl)acetic acid

생성물 1

HCID 87134254N-methoxy-N-methyl-2-(1-phenylcyclobutyl)acetamide수율 89.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A suspension of Example 68C (2.0 g, 10.5 mmol), N,O-dimethylhydroxylamine hydrochloride (1.5 g, 15.8 mmol), HATU (4.8 g, 12.6 mmol) and triethylamine (2.1 g, 21.0 mmol) in 100 mL dichloromethane was stirred at room temperature overnight. The resulting mixture was diluted with water (100 mL) and the aqueous layer was extracted with dichloromethane (50 mL×3). The combined organic layer was dried over Na2SO4, filtered, and concentrated to afford yellow oil. The crude product was purified by reserve-phase C18 column chromatography (H2O/CH3OH=1:4) to afford desired compound (2.2 g, 9.4 mmol, 89.5%) of title compound. LC-MS: m/e=234.1 (M+H+).

후처리

  1. extractionthe aqueous layer was extracted with dichloromethane (50 mL×3)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford yellow oil
  6. customThe crude product was purified by reserve-phase C18 column chromatography (H2O/CH3OH=1:4)

출처 및 근거

ORD 기록
ord-600fffcf91514aafb52f744ce5a63d84
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156788B2

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