Dicyclohexylcarbodiimide → HCID 68526655, 화합물

HRID 2247641노트

반응식

HRID 2247641 반응식
[Si]([O:8][CH2:9][C:10]1[O:14][C:13]([C:15](=[N:17][OH:18])[NH2:16])=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.[CH:19]1([C:25]2[CH:33]=[CH:32][C:28]([C:29](O)=O)=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C1(N=C=NC2CCCCC2)CCCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.CCOCC.O1CCCC1.O>[CH:19]1([C:25]2[CH:33]=[CH:32][C:28]([C:29]3[O:18][N:17]=[C:15]([C:13]4[O:14][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=4)[N:16]=3)=[CH:27][CH:26]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

참가 물질

9

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 883374-Cyclohexylbenzoic acidHCID 2724141Tetrabutylammonium FluorideHCID 866202115-({[t-Butyl(dimethyl)silyl]oxy}methyl)-N'-hydroxyfuran-2-carboximidamide

생성물 1

HCID 68526655HCID 68526655, 화합물수율 81%

시약·촉매·용매 4

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-N′-hydroxyfuran-2-carboximidamide (0.19 g, 0.70 mmol) that was obtained in Example 2 (2b), 4-cyclohexylbenzoic acid (0.16 g, 0.77 mmol), and N,N′-dicyclohexylcarbodiimide (0.17 g, 0.84 mmol) in dichloromethane (1.5 ml) was stirred for 1 hour. After stirring, the reaction mixture was diluted with ether, and insoluble materials were removed by filtration with Celite, and then the filtrate was evaporated in vacuo. Subsequently, to a solution of the residue obtained in tetrahydrofuran (1.0 ml) was added tetrabutylammonium fluoride (a 1.0 M solution in tetrahydrofuran, 1.1 ml, 1.1 mmol) with stirring, and the resulting mixture was stirred at 60° C. for 1 hour. After stirring, the reaction mixture was poured into water (20 ml) to quench the reaction and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1) as the eluent to afford the title compound (0.18 g) in a yield of 81% as a white crystalline solid.

후처리

  1. stirringAfter stirring
  2. customwere removed by filtration with Celite
  3. customthe filtrate was evaporated in vacuo
  4. customSubsequently, to a solution of the residue obtained in tetrahydrofuran (1.0 ml)
  5. stirringwith stirring
  6. stirringthe resulting mixture was stirred at 60° C. for 1 hour
  7. stirringAfter stirring
  8. customto quench
  9. customthe reaction
  10. extractionextracted with ether
  11. washThe extract was washed with a saturated aqueous solution of sodium chloride
  12. dry with materialdried over magnesium sulfate
  13. filtrationAfter filtration
  14. customthe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-d51d45d376004d03ae01720d3f99ff56
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687491B2

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