1,2-Dichloroethane → HCID 72756603, compound

HRID 516977Notes

Reaction equation

HRID 516977 reaction equation
[CH2:1]([CH:4]([CH2:19][CH2:20][CH3:21])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16](O)=[O:17])=[CH:10][CH:9]=1)=[O:6])[CH2:2][CH3:3].C(Cl)CCl.[OH2:26].OC1C2N=NNC=2C=CC=1.Cl.[NH2:38]O>CN(C=O)C>[OH:26][NH:38][C:16](=[O:17])[CH:15]=[CH:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:5](=[O:6])[CH:4]([CH2:19][CH2:20][CH3:21])[CH2:1][CH2:2][CH3:3])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 443297Hydroxyamine hydrochlorideHCID 687996583-{4-[(2-Propylpentanoyl)amino]phenyl}prop-2-enoic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 72756603HCID 72756603, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[4-(2-propyl-pentanoylamino)-phenyl]-acrylic acid (100 mg, 0.35 mmol) in dry DMF (3 mL) was added EDC (79 mg, 0.53 mmol) and hydroxybenzotriazole hydrate (HOBT) (62 mg, 0.46 mmol) under nitrogen. The mixture was stirred for 1 h, hydroxylamine hydrochloride (27.4 mg, 0.39 mmol) and TEA (54 μL) were added, stirred for additional 12 h, concentrated under vacuum, and ethyl acetate (40 mL) and saturated NaHCO3 solution (15 mL) were added. The organic phase was separated, and washed consecutively with water and saturated brine. 20 mL each. The organic layer was dried over Na2SO4, and concentrated under vacuum. The crude product was purified by flash chromatography [ethyl acetate-MeOH (9:1)], yielding compound 10 (45 mg, 40% yield) as white solid. 1H NMR (DMSO-d6) δ 10.69 (s, 1H), 10.07 (s, 1H), 9.00 (s, 1H), 7.67 (d, J=7.9 Hz, 2H), 7.53 (d, J=8.4 Hz, 2H), 7.39 (d, J=15.6 Hz, 1H), 6.39 (d, J=15.3 Hz, 1H), 2.40 (m, 1H), 1.7-1.1 (m, 8H), 0.87 (t, 6H); HRMS: exact mass of (M+Na)+, 327.167911 amu; observed mass of (M+Na)+, 327.16809 amu; anal. (C17H24N2O3) C, H, N.

Workup

  1. stirringstirred for additional 12 h
  2. concentrationconcentrated under vacuum, and ethyl acetate (40 mL) and saturated NaHCO3 solution (15 mL)
  3. additionwere added
  4. customThe organic phase was separated
  5. washwashed consecutively with water and saturated brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by flash chromatography [ethyl acetate-MeOH (9:1)]

Sources & evidence

ORD record
ord-abeb55c299ff4f4fa271e61288724cbc
Source dataset
uspto-grants-2015_08
Patent number
US09115090B2

Reaction notes

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