Potassium Carbonate → HCID 59146135, 화합물

HRID 1512782노트

반응식

HRID 1512782 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[CH:26]=O)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Cl.[NH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].[OH-].[Na+].C([O-])([O-])=O.[K+].[K+]>C(O)C.CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[CH2:26][NH:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 591461517-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole-3-carbaldehyde

생성물 1

HCID 59146135HCID 59146135, 화합물수율 27.8%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 702Ethanol용매2회

실험 절차

7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole-3-carbaldehyde (D71) (381 mg) and ethyl glycinate hydrochloride (223 mg) were added to a solution of NaOH (27 mg) in ethanol (20 mL), followed by addition of AcOH (3 mL). Under stirring NaBH3CN (50 mg) in ethanol (2 mL) was added dropwise. The reaction mixture was stirred at room temperature overnight and then basified to pH 9 by K2CO3 solution. The mixture was concentrated and EtOAc (50 mL) was added. The organic layer was separated and washed with water and brine. After the solvent was evaporated off the residue was purified by Mass Directed AutoPrep to afford ethyl N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}glycinate (D73) (130 mg) as a yellow solid. δH (DMSO-d6, 400 MHz): 1.20 (3H, t), 1.38 (6H, d), 3.48 (2H, s), 4.03 (2H, s), 4.12 (2H, q), 4.88-4.94 (1H, m), 7.25 (1H, t), 7.44 (1H, d), 7.46 (1H, d), 7.96 (1H, t), 8.22 (1H, dd), 8.39 (1H, d), 11.00 (1H, s).

후처리

  1. concentrationThe mixture was concentrated
  2. additionEtOAc (50 mL) was added
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. customAfter the solvent was evaporated off the residue
  6. customwas purified by Mass Directed AutoPrep

출처 및 근거

ORD 기록
ord-ef3b9a413b684d6897fe260f00621c4e
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217028B2

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