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1,1'-Carbonyldiimidazole → (R)-3-(6-Methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl)-3-phenyl-propionic acid ethyl ester

HRID 2175173
ノート
印刷プレビュー

反応式

HRID 2175173 の反応式
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([NH2:20])=[CH:18][N:17]=[C:16]([CH3:21])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].C1N=CN([C:28](N2C=NC=C2)=[O:29])C=1>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C@@H:6]([N:13]1[C:14]2[CH:15]=[C:16]([CH3:21])[N:17]=[CH:18][C:19]=2[NH:20][C:28]1=[O:29])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 58497452(R)-3-(5-Amino-2-methyl-pyridin-4-ylamino)-3-phenyl-propionic acid ethyl ester

生成物 1

HCID 58497428(R)-3-(6-Methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl)-3-phenyl-propionic acid ethyl ester収率 75.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate
溶媒

実験手順

To a solution of (R)-3-(5-amino-2-methyl-pyridin-4-ylamino)-3-phenyl-propionic acid ethyl ester (594 mg, 1.98 mmol) in THF (20 mL) was added CDI (483 mg, 2.98 mmol). The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 484 mg (75%) of the title compound as light brown solid. LCMS, M++1, m/z: 326.85.

後処理

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel prep TLC

出典と根拠

ORDレコード
ord-80673a0e08de4572b44dc569d9d9ae3f
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09062056B2

反応ノート

読み込み中…

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