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

HRID 1510978
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HRID 1510978 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ae57e28fcd94a3fa5cf23ca89ab0b48
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08212052B2

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