1,2-Dichloroethane → HCID 58460184, compound

HRID 1946493Notes

Reaction equation

HRID 1946493 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.N.[Cl:14][C:15]1[CH:16]=[C:17]([CH2:22][N:23]2[C:27]3[CH:28]([CH2:31][C:32](O)=[O:33])[CH2:29][CH2:30][C:26]=3[N:25]=[C:24]2[CH:35]([CH3:37])[CH3:36])[CH:18]=[CH:19][C:20]=1[Cl:21]>CN(C1C=CN=CC=1)C.ClCCl>[Cl:14][C:15]1[CH:16]=[C:17]([CH2:22][N:23]2[C:27]3[CH:28]([CH2:31][C:32]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:33])[CH2:29][CH2:30][C:26]=3[N:25]=[C:24]2[CH:35]([CH3:37])[CH3:36])[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 244Benzyl AlcoholHCID 67434388HCID 67434388, compound

Product 1

HCID 58460184HCID 58460184, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl alcohol (0.193 mL), DMAP (16.96 mg) and EDC (195 mgl) were successively added to a stirring solution of Example 9 (340 mg) in dichloromethane (5 mL) cooled at 0° C. under nitrogen. The RM was warmed to room temp and left stirring under nitrogen atm. overnight. The reaction mixture was partitioned between dichloromethane (10 mL) and water (10 mL). The aqueous phase was again extracted with DCM (20 ml). The 2 phases were separated; the organic extract was dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (380 mg). LC/MS MH+ 457, 459, Rt 3.55 min (5 minute run).

Workup

  1. temperatureThe RM was warmed to room temp
  2. waitleft
  3. customovernight
  4. customThe reaction mixture was partitioned between dichloromethane (10 mL) and water (10 mL)
  5. extractionThe aqueous phase was again extracted with DCM (20 ml)
  6. customThe 2 phases were separated
  7. extractionthe organic extract
  8. customwas dried (hydrophobic frit)
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified on silica using a cyclohexane
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-60477f35d3294237bd9672ab7f933e06
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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