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

HRID 1749157
ノート
印刷プレビュー

反応式

HRID 1749157 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-600fffcf91514aafb52f744ce5a63d84
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09156788B2

反応ノート

読み込み中…

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