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

HRID 1710336ノート

反応式

HRID 1710336 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-a26a6cb982be419891de9650f07f65f0
出典データセット
uspto-grants-2010_09
特許番号
US07790707B2

反応ノート

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