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Hydrochloric Acid → HCID 90100317, 화합물

HRID 2207302
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HRID 2207302 반응식
C(OC(=O)[N:7]([S:13]([C:16]1[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=1)(=[O:15])=[O:14])[C:8]1[S:9][CH:10]=[CH:11][N:12]=1)(C)(C)C.C([Li])CCC.[O:29]1[CH:33]=[CH:32][C:31]([C:34]2[N:41]=[CH:40][CH:39]=[CH:38][C:35]=2[CH:36]=[O:37])=[CH:30]1.Cl>O1CCCC1.O.C(OCC)(=O)C>[O:29]1[CH:33]=[CH:32][C:31]([C:34]2[C:35]([CH:36]([OH:37])[C:19]3[CH:18]=[CH:17][C:16]([S:13]([NH:7][C:8]4[S:9][CH:10]=[CH:11][N:12]=4)(=[O:14])=[O:15])=[CH:21][CH:20]=3)=[CH:38][CH:39]=[CH:40][N:41]=2)=[CH:30]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 86672843HCID 86672843, 화합물HCID 118522199HCID 118522199, 화합물HCID 178418339Butyllithium

생성물 1

HCID 90100317HCID 90100317, 화합물수율 11.2%

시약·촉매·용매 3

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매
2회
HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

100 mg (0.28 mmol) of tert-butyl((4-fluorophenyl)sulfonyl)(thiazol-2-yl)carbamate was dissolved in 5 mL of tetrahydrofuran under nitrogen gas, and cooled to −78° C. After adding 0.26 mL (0.42 mmol) of n-butyllithium (1.6 M in tetrahydrofuran) slowly, the mixture was stirred for 30 minutes as maintaining −78° C. 23 mg (0.13 mmol) of 2-(furan-3-yl)nicotinaldehyde was dissolved in 0.5 mL of tetrahydrofuran, and added to the above reacting solution. As warming from −78° C. to room temperature, the reacting solution was stirred for 24 hours. Ethyl acetate and water/1 N-hydrochloride were added to the reacting solution, and it was stirred. After separating layers, the organic layer only was collected and concentrated under reduced pressure. The obtained residue was separated by column chromatography (developing solvent, hexane:ethyl acetate=1:1) to obtain 6 mg (5.2% yield) of the title compound.

후처리

  1. temperatureas maintaining −78° C
  2. additionadded to the
  3. temperatureAs warming from −78° C. to room temperature
  4. stirringthe reacting solution was stirred for 24 hours
  5. stirringwas stirred
  6. customAfter separating layers
  7. customthe organic layer only was collected
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was separated by column chromatography (developing solvent, hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-c0da594b32764e7aa34e8349de3cb206
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09376429B2

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