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1,2-Dichloroethane → 7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid ((R)-1-benzyl-2-benzyloxycarbamoylethyl)amide

HRID 1510978
ノート
印刷プレビュー

反応式

HRID 1510978 の反応式
[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:11][CH2:12][CH3:13])[NH:10][C:6]=2[CH:5]=[C:4]([C:14]([OH:16])=O)[CH:3]=1.[NH2:17][C@H:18]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:19][C:20]([NH:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.C(Cl)Cl.C(N(CC)CC)C>[CH2:31]([C@@H:18]([NH:17][C:14]([C:4]1[CH:3]=[C:2]([CH3:1])[C:7]2[N:8]=[C:9]([CH2:11][CH2:12][CH3:13])[NH:10][C:6]=2[CH:5]=1)=[O:16])[CH2:19][C:20](=[O:21])[NH:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 102628317-Methyl-2-propyl-1H-benzimidazole-5-carboxylic acidHCID 14134575(R)-3-amino-N-benzyloxy-4-phenylbutyramide

生成物 1

HCID 441584617-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid ((R)-1-benzyl-2-benzyloxycarbamoylethyl)amide収率 41.2%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of 7-methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid (164 mg, 752 μmol) and (R)-3-amino-N-benzyloxy-4-phenylbutyramide (TFA salt: 300 mg, 754 μmol) in DMF (10 mL) containing triethylamine (210 μL), was added HOBt (151 μg, 755 μmol) and EDC (151 mg, 788 μmol). The mixture was stirred at room temperature overnight and concentrated in vacuo, yielding a pale brown residue. The residue was dissolved in DCM (100 mL) and washed sequentially with 1M H3PO4, a saturated NaHCO3 solution, and saturated aqueous NaCl. The organic layer was collected, dried over MgSO4, and concentrated to afford the title compound as a pale yellow oil (150 mg; 41% yield), which was used without further treatment. ESMS [M+H]+ calcd for C29H32N4O3, 485.26. found 485.5.

後処理

  1. concentrationconcentrated in vacuo
  2. customyielding a pale brown residue
  3. washwashed sequentially with 1M H3PO4
  4. customThe organic layer was collected
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-5ae57e28fcd94a3fa5cf23ca89ab0b48
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08212052B2

反応ノート

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