1,2-Dichloroethane → HCID 69734264, compound

HRID 1062899Notes

Reaction equation

HRID 1062899 reaction equation
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[C:5]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=O)=[O:6])[CH2:2][CH3:3].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:34][O:35][C:36](=[O:43])[C@H:37]([CH2:39][CH:40]([CH3:42])[CH3:41])[NH2:38].CN1CCOCC1>CN(C=O)C>[CH2:16]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([NH:38][C@@H:37]([CH2:39][CH:40]([CH3:42])[CH3:41])[C:36]([O:35][CH3:34])=[O:43])=[O:12])=[O:6])[CH2:17][CH3:18]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 1827693-(Dipropylcarbamoyl)benzoic acidHCID 2723695Leucine methyl ester hydrochloride

Product 1

HCID 69734264HCID 69734264, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-[(Dipropylamino)carbonyl]benzoic acid, (1.24 g, 5 mmol) is combined with EDC (0.95 g, 5 mmol) and HOBT (0.69, 5.1 mmol) in 10 mL of DMF and stirred under nitrogen for 1 h. This solution is then added to a solution of L-leucine methyl ester hydrochloride (0.9 g, 5 mmol) and 0.55 mL (5 mmol) of 4-methylmorpholine in 5 mL of DMF. The reaction is continued for 3 days at ambient temperature. It is then quenched with 1 N KH2PO4 and diluted with ethyl acetate. The organic phase is washed with water, 1 N NaHCO3, and brine, and dried over Na2SO4. Concentration and chromatography over silica gel, eluting with 50% ethyl acetate in heptane, affords 1.65 g (4.4 mmol, 88%) of the title compound as a colorless oil which crystallizes on standing. 1H NMR (CDCl3) δ 7.82 (m, 1H), 7.77 (s, 1H), 7.51-7.44 (m, 2H), 6.65 (d, J=8 Hz, 1H), 4.84 (m, 1H), 3.77 (s, 3H), 3.46 (br t, 2H), 3.14 (br t, 2H), 1.78-1.65 (m, 5H), 1.53 (m, 2H), 0.99 (m, 9H), 0.75 (br t, 3H).

Workup

  1. waitThe reaction is continued for 3 days at ambient temperature
  2. customIt is then quenched with 1 N KH2PO4
  3. additiondiluted with ethyl acetate
  4. washThe organic phase is washed with water, 1 N NaHCO3, and brine
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration and chromatography over silica gel
  7. washeluting with 50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-a202dae41a2e4165a0f4f78286043e9f
Source dataset
uspto-grants-2005_11
Patent number
US06962934B2

Reaction notes

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