Dichloromethane → {1-[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-2-yl]-ethyl}-carbamic Acid Tert-Butyl Ester

HRID 1827332Notes

Reaction equation

HRID 1827332 reaction equation
NC1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[CH:9][CH:8]=1)=O.C1C2C(C[O:34][C:35](N[C@@H](C(O)=O)C)=[O:36])C3C(=CC=CC=3)C=2C=CC=1.CCN=C=N[CH2:48][CH2:49][CH2:50]N(C)C.C1C=C[C:57]2[N:62](O)N=[N:60][C:58]=2[CH:59]=1.[CH2:64](Cl)Cl>>[C:49]([O:36][C:35](=[O:34])[NH:60][CH:58]([C:57]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH3:15])=[CH:11][CH:12]=2)[C:4]2[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=2[N:62]=1)[CH3:59])([CH3:50])([CH3:64])[CH3:48]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7501792-amino-N-(4-ethoxyphenyl)benzamideHCID 2724627(2R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid

Product 1

HCID 23401405{1-[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-2-yl]-ethyl}-carbamic Acid Tert-Butyl Ester

Procedure

To a mixture of compound XX (7.68 g, 30 mmol) and N-(9-fluorenylmethyloxycarbonyl)-D-alanine (10.26 g, 33 mmol) in CH2Cl2 (150 mL), was added EDAC (8.63 g, 45 mmol) and HOBt (1.38 g, 9 mmol). After stirring at room temperature overnight, the resulting solid was filtered and washed with ethyl ether to yield compound XXI (14.50 g). 1H NMR (CDCl3) 1.37 (t, 3H, J=7.0 Hz), 1.48 (d, 3H, J=7.2 Hz), 3.89 (m, 2H), 4.26 (m, 2H), 4.45 (m, 2H), 5.50 (m, 1H), 6.76 (m, 2H), 7.17 (t, 1H, J=7.3 Hz), 7.25–7.76 (m, 12H), 8.62 (d, 1H, J=8.8 Hz), 11.43 (s, 1H). MS(ESI+) 550.3 (MH+).

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with ethyl ether

Sources & evidence

ORD record
ord-6817f0e1259d4380b0c994d49717f210
Source dataset
uspto-grants-2006_05
Patent number
US07053215B2

Reaction notes

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