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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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tert-Butyldimethylsilyl chloride → 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]benzoic acid

HRID 1990267
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HRID 1990267 반응식
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N:9]1([C:13]([C:15]2[CH:16]=[C:17]([Cl:36])[C:18]([O:21][C:22]3[CH:23]=[C:24]([CH:28]=[C:29]([O:31][C@@H:32]([CH3:35])[CH2:33][OH:34])[CH:30]=3)[C:25]([OH:27])=[O:26])=[N:19][CH:20]=2)=[O:14])[CH2:12][CH2:11][CH2:10]1.N12CCCN=C1CCCCC2>C(#N)C>[N:9]1([C:13]([C:15]2[CH:16]=[C:17]([Cl:36])[C:18]([O:21][C:22]3[CH:23]=[C:24]([CH:28]=[C:29]([O:31][C@@H:32]([CH3:35])[CH2:33][O:34][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:30]=3)[C:25]([OH:27])=[O:26])=[N:19][CH:20]=2)=[O:14])[CH2:12][CH2:11][CH2:10]1
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참가 물질

5

반응물 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 591271743-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzoic acid

생성물 1

HCID 536296873-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]benzoic acid수율 60.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

tert-Butyldimethylsilyl chloride (2.78 g, 18.4 mmol) was added to a mixture of 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzoic acid (3.74 g, 9.19 mmol) and 1,8-diazabicyclo(5,4,0)undec-7-ene (2.75 mL, 7.36 mmol) in acetonitrile (40 mL) and stirred at RT for 24 hours. The solvent was removed in vacuo and water (80 mL) added to the resultant oil. The mixture was adjusted to pH 10 with 1M sodium bicarbonate solution and washed with ether to remove any impurities. The aqueous layer was adjusted to pH 3 with 1M citric acid and extracted into ethyl acetate (2×100 mL). The combined organics were washed with brine (50 mL), dried (MgSO4), filtered and reduced in vacuo to give the desired compound as a white foam (2.9 g).

후처리

  1. customThe solvent was removed in vacuo and water (80 mL)
  2. additionadded to the resultant oil
  3. washwashed with ether
  4. customto remove any impurities
  5. extractionextracted into ethyl acetate (2×100 mL)
  6. washThe combined organics were washed with brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-3e56299181f546f796eead76729945f0
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07642259B2

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