Acetic Acid → HCID 68579161, 화합물

HRID 643500노트

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HRID 643500 반응식
[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24](Cl)[N:23]=3)[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C-]#N.[K+].[N:33]12CCN(CC1)C[CH2:34]2.CC(O)=O>O.CS(C)=O>[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]([C:34]#[N:33])[N:23]=3)[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 9237DabcoHCID 86622894HCID 86622894, 화합물

생성물 1

HCID 68579161HCID 68579161, 화합물

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

A mixture of [3′-(2-chloro-pyrimidin-4-yloxy)-biphenyl-4-ylmethyl]-carbamic acid tert-butyl ester (161 mg), potassium cyanide (76 mg) and 1,4-diazabicyclo[2,2,2]octane (13 mg) in water (0.4 ml) and DMSO (2 ml) is left at 5° C. for 4 h. This mixture is acidified with AcOH to pH 4-5, quenched with brine and extracted twice with diethyl ether. The combined organic phases are dried over sodium sulfate, the solvent is evaporated and the crude product is purified on silica (15 g) with cyclohexane/EtOAc=5/1 to afford pure [3′-(2-cyano-pyrimidin-4-yloxy)-biphenyl-4-ylmethyl]-carbamic acid tert-butyl ester.

후처리

  1. customquenched with brine
  2. extractionextracted twice with diethyl ether
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. customthe solvent is evaporated
  5. customthe crude product is purified on silica (15 g) with cyclohexane/EtOAc=5/1

출처 및 근거

ORD 기록
ord-e94a73e1394a40889c7b56d585feaeb0
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700605B2

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