1,2-Dichloroethane → HCID 15951585, compound

HRID 1642258Notes

Reaction equation

HRID 1642258 reaction equation
[C:1]([NH:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][C:7]([OH:9])=O)(=[O:3])[CH3:2].C(Cl)CCl.C(N(CC)CC)C.[Cl:27][C:28]1[CH:41]=[CH:40][C:31]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[NH2:39])=[CH:30][CH:29]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:27][C:28]1[CH:41]=[CH:40][C:31]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[NH:39][C:7](=[O:9])[CH2:6][CH:5]([NH:4][C:1](=[O:3])[CH3:2])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 760102-(4-Chlorophenoxy)anilineHCID 34808823-Acetamido-3-phenylpropanoic acid

Product 1

HCID 15951585HCID 15951585, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a pre-stirred solution of N-acetyl-3-phenyl-β-alanine (104 mg, 0.50 mmol), EDC (265 mg, 1.38 mmol), triethylamine (70 mg, 0.69 mmol) and DMAP (6 mg, 0.046 mmol) in anhydrous DCM (25 ml), was added 2-(4-chlorophenoxy)phenylamine (100 mg, 0.46 mmol). This mixture was then allowed to stir at room temperature for 14 h. The reaction mixture was washed with 2.5M NaOH (20 ml), 2M HCl (20 ml) and the organics were then dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (eluant; DCM to 9:1 DCM:MeOH) then proceeded to afford the desired product as an off-white solid (58.9 mg, 31%). 1H NMR (270 MHz, CDCl3): δ 2.03 (3H, s, CH3), 2.83-2.99 (2H, m, CH2), 5.30-5.40 (1H, m, CH), 6.73-6.77 (1H, dd, J=1.5, 8.2 Hz, Ar—H), 6.83-6.86 (2H, m, Ar—H), 6.95-7.03 (1H, td, J=1.7, 7.9 Hz, Ar—H), 7.05-7.11 (1H, td, J=1.7, 7.9 Hz, Ar—H), 7.19-7.30 (7H, m, Ar—H), 7.60 (1H, br s, Ar—H), 8.22-8.25 ppm (1H, dd, J=1.5, 8.0 Hz, Ar—H). LCMS: M+H, 409.44 HPLC: 98.66% (2.268 mins, isocratic 90% acetonitrile, 10% water at 1 ml/min).

Workup

  1. washThe reaction mixture was washed with 2.5M NaOH (20 ml), 2M HCl (20 ml)
  2. dry with materialthe organics were then dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (eluant; DCM to 9:1 DCM:MeOH)

Sources & evidence

ORD record
ord-fb98fe3ef37e47e7a1c0c7aab291c9be
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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