1,2-Dichloroethane → HCID 10159934, compound

HRID 1830166Notes

Reaction equation

HRID 1830166 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8]([CH2:12][S:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:15])=[O:14])[C:9](O)=[O:10])[CH:2]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:44][CH2:45][C:46]#[N:47].CN1CCOCC1>>[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8]([CH2:12][S:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:15])=[O:14])[C:9]([NH:47][CH2:46][C:45]#[N:44])=[O:10])[CH:2]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 11491918Aminoacetonitrile hydrochlorideHCID 22054068HCID 22054068, compound

Product 1

HCID 10159934HCID 10159934, compound

Procedure

3-Biphenyl-3-yl-2-benzylsulfonylmethyl-propionic acid (300 mg, 0.76 mmol), prepared as in Reference 9, was combined with EDC (300 mg, 1.57 mmol), HOBt (300 mg, 1.96 mmol), and aminoacetonitrile hydrochloride (150 mg, 1.6 mmol). Dichloromethyl (4 mL) was added and then 4-methylmorpholine (0.5 mL). The mixture was stirred at ambient temperature for 2 hours. After dilution with ethyl acetate (150 mL), the solution was washed with water (30 mL), saturated aqueous NaHCO3 solution and brine, dried with magnesium sulfate and evaporated under vacuum. The product, 3-biphenyl-3-yl-N-cyanomethyl-2-benzylsulfonylmethyl-propionamide (273 mg), was crystallized from ethyl acetate/hexane as a white solid; 1H NMR: (DMSO) 8.87 (t, J=5.5 Hz, 1H), 7.68–7.14 (m, 14H), 4.45 (d, J=13.8 Hz, 1H), 4.38 (d, J=13.8 Hz, 1H), 4.13 (m, 2H), 3.49 (dd, J=9.4 Hz, J=14.1 Hz, 1H), 3.28–3.11 (m, 1H), 3.04–2.76 (m, 3H). MS: (M++1) 433.

Workup

  1. additionDichloromethyl (4 mL) was added
  2. washAfter dilution with ethyl acetate (150 mL), the solution was washed with water (30 mL), saturated aqueous NaHCO3 solution and brine
  3. dry with materialdried with magnesium sulfate
  4. customevaporated under vacuum
  5. customThe product, 3-biphenyl-3-yl-N-cyanomethyl-2-benzylsulfonylmethyl-propionamide (273 mg), was crystallized from ethyl acetate/hexane as a white solid

Sources & evidence

ORD record
ord-dc99dbc285774028b8f2a0997076e83e
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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