Isopropylamine → 4-(3-Hydroxy-1-azetidinyl)-N-(1-methylethyl)benzamide

HRID 1049133노트

반응식

HRID 1049133 반응식
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2[CH:13]=CC=C[C:11]=2N=N1.[OH:28][CH:29]1[CH2:32][N:31]([C:33]2[CH:41]=[CH:40][C:36]([C:37]([OH:39])=O)=[CH:35][CH:34]=2)[CH2:30]1.CC(N)C.C(N(CC)C(C)C)(C)C>ClCCl>[OH:28][CH:29]1[CH2:30][N:31]([C:33]2[CH:34]=[CH:35][C:36]([C:37]([NH:8][CH:12]([CH3:13])[CH3:11])=[O:39])=[CH:40][CH:41]=2)[CH2:32]1

참가 물질

6

반응물 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 838182714-(3-Hydroxyazetidin-1-yl)benzoic acid

생성물 1

HCID 711435344-(3-Hydroxy-1-azetidinyl)-N-(1-methylethyl)benzamide수율 94.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (4.64 g, 10.5 mmol, from Aldrich) was added to a mixture of 4-(3-hydroxyazetidin-1-yl)benzoic acid (1.93 g, 10.0 mmol), 2-propanamine (4.26 mL, 50.0 mmol) and N,N-diisopropylethylamine (3.88 g, 30.0 mmol) in dichloromethylene (10 mL). The mixture was stirred at room temperature for 2 h, and diluted with dichloromethane. The mixture was washed with aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column eluting with ethyl acetate in hexane (gradient: 0-50%) to afford the desired product (2.21 g, 94.3%). LCMS cacld. for C13H19N2O2 (M+1)+: m/z=235.1. Found: 235.1.

후처리

  1. washThe mixture was washed with aqueous NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on a silica gel column
  6. washeluting with ethyl acetate in hexane (gradient: 0-50%)

출처 및 근거

ORD 기록
ord-4c6b88eae32f4303b98d739f894d0c71
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382231B2

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