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Triethylamine → (S)-methyl 2-(6-((2',6'-dimethyl-4'-((1-propionylazetidin-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 2280662
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HRID 2280662 반응식
FC(F)(F)C(O)=O.[NH:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[C:17]([CH3:19])[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][O:27][C:28]4[CH:41]=[CH:40][C:31]5[C@H:32]([CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH2:33][O:34][C:30]=5[CH:29]=4)[CH:21]=3)=[C:15]([CH3:42])[CH:14]=2)[CH2:9]1.C(N(CC)CC)C.[C:50](Cl)(=[O:53])[CH2:51][CH3:52]>ClCCl>[CH3:19][C:17]1[CH:18]=[C:13]([O:12][CH:10]2[CH2:11][N:8]([C:50](=[O:53])[CH2:51][CH3:52])[CH2:9]2)[CH:14]=[C:15]([CH3:42])[C:16]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][O:27][C:28]2[CH:41]=[CH:40][C:31]3[C@H:32]([CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH2:33][O:34][C:30]=3[CH:29]=2)[CH:21]=1
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 131733506(S)-Methyl 2-(6-((4'-(azetidin-3-yloxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 2,2,2-trifluoroacetate

생성물 1

HCID 117699335(S)-methyl 2-(6-((2',6'-dimethyl-4'-((1-propionylazetidin-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate수율 94.4%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

The crude (S)-methyl 2-(6-((4′-(azetidin-3-yloxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 2,2,2-trifluoroacetate 14c (40 mg, 0.09 mmol) was dissolved in 3 mL of dichloromethane, followed by addition of triethylamine (0.1 mL, 0.26 mmol) and propionyl chloride (11 mL, 0.13 mmol) successively. The reaction solution was stirred for 12 hours. The resulting solution was mixed with 10 mL of dichloromethane, washed with saturated sodium chloride solution (5 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound (S)-methyl 2-(6-((2′,6′-dimethyl-4′-((1-propionylazetidin-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 14d (45 mg) as a yellow oil, which was directly used in the next step without further purification.

후처리

  1. washwashed with saturated sodium chloride solution (5 mL)
  2. dry with materialdried with anhydrous magnesium sulphate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-161501b0f90848f195e2a43fb2e18693
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09139548B2

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