Acetic Acid → 1-(4-(3-(4-tert-Butylphenyl)-2-oxoimidazolidin-1-yl)benzyl)azetidine-3-carboxylic acid

HRID 1710336노트

반응식

HRID 1710336 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)[C:12]2=[O:24])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[NH:29]1[CH2:32][CH:31]([C:33]([OH:35])=[O:34])[CH2:30]1.C([BH3-])#N.[Na+]>ClCCl.CO.CS(C)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:20][N:29]4[CH2:32][CH:31]([C:33]([OH:35])=[O:34])[CH2:30]4)=[CH:22][CH:23]=3)[C:12]2=[O:24])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 931923-azetidinecarboxylic AcidHCID 5003444Sodium cyanoborohydrideHCID 594568184-(3-(4-tert-Butylphenyl)-2-oxoimidazolidin-1-yl)benzaldehyde

생성물 1

HCID 247719691-(4-(3-(4-tert-Butylphenyl)-2-oxoimidazolidin-1-yl)benzyl)azetidine-3-carboxylic acid수율 10%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 21226129Dichloromethane methanol용매

실험 절차

A mixture of 4-(3-(4-tert-butylphenyl)-2-oxoimidazolidin-1-yl)benzaldehyde (32 mg, 0.1 mmol), acetic acid (50 μl) and azetidine-3-carboxylic acid (13 mg, 0.13 mmol) in dichloromethane/MeOH (1:1, 5 mL) was stirred at room temperature for 1 hour. Sodium cyanoborohydride (3.5 mg, 0.05 mmol) was added and the reaction mixture was stirred for 6 hour at room temperature. After concentration of solvent under reduced pressure, the resulting residue was dissolved in dimethylsulfoxide, filtered and purified by reverse phase preparative HPLC (Phenomenex reverse phase Luna 5u C18(2) column, 60×21.2 mm ID, mobile phase: A=0.05% TFA in water; B=0.05% TFA in acetonitrile. The flow rate was 10-12 mL/min) to yield the title product 4 mg (10%): 1H NMR (400 MHz, CDOD3) δ 7.72 (d, 2H), 7.51-7.40 (m, 6H), 4.33 (s, 2H), 4.28 (m, 4H), 4.02 (s, 4H), 3.64 (m, 1H), 1.32 (s, 9H). MS (ESI) m/z: Calculated: 407.22; Observed: 408.00 (M++1).

후처리

  1. stirringthe reaction mixture was stirred for 6 hour at room temperature
  2. filtrationfiltered
  3. custompurified by reverse phase preparative HPLC (Phenomenex

출처 및 근거

ORD 기록
ord-a26a6cb982be419891de9650f07f65f0
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790707B2

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