1,2-Dichloroethane → HCID 70234737, compound

HRID 2098459Notes

Reaction equation

HRID 2098459 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[C:10]([CH3:13])([CH3:12])[CH3:11])=[O:7])([CH3:4])[CH3:3].[C@H:17]12[CH2:23][C@H:20]([NH:21][CH2:22]1)[CH2:19][N:18]2[C:24]([C:26]1[NH:30][C:29]2[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=2[N:27]=1)=[O:25].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O>[NH:27]1[C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=[C:26]1[C:24]([N:18]1[CH2:19][C@@H:20]2[CH2:23][C@H:17]1[CH2:22][N:21]2[C:14]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]([CH3:11])([CH3:12])[CH3:13])=[O:16])=[O:25]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acidHCID 58286559HCID 58286559, compound

Product 1

HCID 70234737HCID 70234737, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-{[(1,1-dimethylethyl)oxy]carbonyl}-3-methyl-L-valine (3 g, 13 mmol) (2-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylcarbonyl]-1H-benzimidazole (3 g, 12.4 mmol), EDC (2.8 g, 14.8 mmol), HOBt (334 mg, 2.5 mmol), NMM (3.7 g, 37.1 mmol) in CH2Cl2 (50 mL) was stirred at room temperature for 18 h. The reaction was diluted with water and CH2Cl2 then washed with sat. NaHCO3 (50 mL) and brine (50 mL). The solution was dried over anhydrous Na2SO4 and concentrated to give the title compound (5.6 g) as a pale yellow solid. LCMS (m/z): 456.3 (M+H).

Workup

  1. washthen washed with sat. NaHCO3 (50 mL) and brine (50 mL)
  2. dry with materialThe solution was dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-761bb1373f174e769e46c18e9216385a
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

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