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

HRID 1895506Notes

Reaction equation

HRID 1895506 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-721f8970b16c4ad4b65d0d424f16a83b
Source dataset
uspto-grants-2013_08
Patent number
US08513432B2

Reaction notes

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