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HCID 86648519, 화합물 → Ethyl 2-[bis(tert-butoxycarbonyl)amino]-4-(1-hydroxypropyl)-1,3-thiazole-5-carboxylate

HRID 1424982
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HRID 1424982 반응식
[C:1]([O:5][C:6]([N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:9]1[S:10][C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH:14]=[O:15])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:28]([Mg]Br)[CH3:29]>C(OCC)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([N:8]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[C:9]1[S:10][C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH:14]([OH:15])[CH2:28][CH3:29])[N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

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HCID 86648519HCID 86648519, 화합물HCID 178418443HCID 178418443, 화합물

생성물 1

HCID 67548974Ethyl 2-[bis(tert-butoxycarbonyl)amino]-4-(1-hydroxypropyl)-1,3-thiazole-5-carboxylate수율 33%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 3283Diethyl Ether용매2회

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온도
-78 °C

실험 절차

Ethyl 2-[bis(tert-butoxycarbonyl)amino]-4-formyl-1,3-thiazole-5-carboxylate obtained in Example (62d) (915.5 mg, 2.29 mmol) was dissolved in diethyl ether (30 mL), followed by cooling to −78° C. Then, tetrabutylammonium bromide (890 mg, 2.76 mmol) and ethylmagnesium bromide (1 M solution in THF, 2.8 mL) were added, and the mixture was stirred for one hour. Diethyl ether was added to the reaction solution, and the organic layer was washed with brine and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=91/9, 85/15) to obtain 327.2 mg of the title compound (33%).

후처리

  1. washthe organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentration under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=91/9, 85/15)

출처 및 근거

ORD 기록
ord-51469568ce6f4934873214bfd9a130c4
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08927588B2

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