Diisopropylamine → HCID 18946695, 화합물

HRID 1769198노트

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HRID 1769198 반응식
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26]([OH:28])=[O:27])=[CH:18]1)[CH2:14][CH2:15][CH3:16].C([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]#[N:44])=O.[O:45]1CCC[CH2:46]1>C(OCC)(=O)C.O>[CH2:13]([N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26]([OH:28])=[O:27])=[C:18]1[CH:46]([OH:45])[C:35]1[CH:36]=[CH:31][C:32]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:43]#[N:44])=[CH:33][CH:34]=1)[CH2:14][CH2:15][CH3:16]

참가 물질

8

반응물 5

HCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2회HCID 2519652'-formylbiphenyl-2-carbonitrileHCID 103762901-butylindole-3-carboxylic AcidHCID 178418339Butyllithium

생성물 1

HCID 18946695HCID 18946695, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
-50 °C

실험 절차

To a 3 liter 3-neck flask was added 1 liter of dry tetrahydrofuran and 48.4 ml diisopropylamine. The mixture was cooled to -50° C. under argon, and 216 ml of 1.6M of n-butyllithium (in hexane) was added dropwise over 5 minutes. The mixture was then allowed to warm to -10° C., and then recooled to -40° C. A solution of 30 g of 1-butylindole-3-carboxylic acid in 100 ml dry tetrahydrofuran was added dropwise over 5 minutes. The solution was stirred at -40° to -30° C. for 1 hour, and then recooled to -70° C. At once was added 28.61 g of 2-formyl-2'-cyanobiphenyl, and the mixture was stirred at -70° C. under argon for 2 hours. The mixture then was warmed to -20° C. and 500 ml of water was added while stirring. Ethyl acetate was then added to the mixture and the aqueous layer separated, which was extracted three times with ethyl acetate. The ethyl acetate extracts were combined, washed with 1N HCl, and dried (MgSO4). The solvent was removed under reduced pressure, and the resulting material recrystallized from a mixture of ethyl acetate and hexane, to yield 36.4 g of 1-(n-butyl)-2-[1-hydroxy-1-(2"-cyanobiphenyl-4'yl)methyl]indole-3-carboxylic acid.

후처리

  1. temperatureto warm to -10° C.
  2. customrecooled to -40° C
  3. customrecooled to -70° C
  4. stirringthe mixture was stirred at -70° C. under argon for 2 hours
  5. temperatureThe mixture then was warmed to -20° C.
  6. stirringwhile stirring
  7. customthe aqueous layer separated
  8. extractionwhich was extracted three times with ethyl acetate
  9. washwashed with 1N HCl
  10. dry with materialdried (MgSO4)
  11. customThe solvent was removed under reduced pressure
  12. customthe resulting material recrystallized from a mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-c2c13f24935642b19e75ba89d5375a35
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380739

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