Water → 1-[4-Hydroxy-3-(hydroxymethyl)phenyl]-2-[[6-[3-[3-(phenylmethoxy)-2-pyridinyl]propoxy]hexyl](phenylmethyl)amino]ethanone

HRID 1088720노트

반응식

HRID 1088720 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][OH:13])[CH:6]=1)=[O:4].[C:14]1([CH2:20][O:21][C:22]2[C:23]([CH2:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.CCOCC>C1COCC1>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:38]([CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][CH2:28][C:23]2[C:22]([O:21][CH2:20][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[CH:6][C:7]=1[CH2:12][OH:13]

참가 물질

6

반응물 4

HCID 962WaterHCID 3283Diethyl EtherHCID 113340552-Bromo-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethan-1-oneHCID 54019079N-[6-[3-[3-(phenylmethoxy)-2-pyridinyl]propoxy]hexyl]benzenemethanamine

생성물 1

HCID 221617531-[4-Hydroxy-3-(hydroxymethyl)phenyl]-2-[[6-[3-[3-(phenylmethoxy)-2-pyridinyl]propoxy]hexyl](phenylmethyl)amino]ethanone수율 56.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)phenyl]ethanone (460 mg), N-[6-[3-[3-(phenylmethoxy)-2-pyridinyl]propoxy]hexyl]benzenemethanamine (800 mg) and DEA (485 mg) in THF (15 ml) was left at room temperature overnight. Water (30 ml) and ether (30 ml) were added, the phases were separated and the organic layer was re-extracted with ether (50 ml). The combined extracts were washed with water and brine, dried and concentrated to an oil which was purified by FCC eluting with ethyl acetate/triethylamine (99:1) followed by ethyl acetate/methanol/triethylamine (90:10:1) to give the title compound as an orange oil (620 mg), t.l.c. (ethyl acetate/methanol/triethylamine 80:20:1) Rf 0.66.

후처리

  1. customthe phases were separated
  2. extractionthe organic layer was re-extracted with ether (50 ml)
  3. washThe combined extracts were washed with water and brine
  4. customdried
  5. concentrationconcentrated to an oil which
  6. customwas purified by FCC
  7. washeluting with ethyl acetate/triethylamine (99:1)

출처 및 근거

ORD 기록
ord-1a0a2b06a7af47bd8738b09c5944e96a
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04963564

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