1-Hydroxybenzotriazole → HCID 58677920, compound

HRID 2102224Notes

Reaction equation

HRID 2102224 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.Cl.[CH3:14][NH:15][O:16][CH3:17].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:15]([O:16][CH3:17])[CH3:14])=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27356093-(4-Bromophenyl)propionic acid

Product 1

HCID 58677920HCID 58677920, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 24.95 g 3-(4-bromophenyl)propionic acid, 12.75 g N,O-dimethylhydroxylamine hydrochloride, 27.14 g EDC, and 17.66 g HOBt were added 300 mL DMF and 47.4 mL DIEA. The reaction mixture was stirred at room temperature for 17 hours and then poured into 700 mL ice water, extracted with 5×200 mL EtOAc. The combined EtOAc solution was washed with 200 mL 5% NaHCO3, 4×200 mL water, and 200 mL saturated brine, dried over Na2SO4, and concentrated under reduced pressure to give crude product as a yellow oil. It was purified on silica gel using 35-55% EtOAc in hexanes to give the title compound as yellowish oil. 1H NMR (CDCl3, 500 MHz) δ 7.40˜7.43 (m, 2H), 7.11˜7.14 (m, 2H), 3.63 (s, 3), 3.19 (s, 3H), 2.93 (t, J=7.8 Hz, 2H), 2.73 (t, J=7.7 Hz, 2H). LC-MS: 1.77 min. (M+H=272.1/274).

Workup

  1. extractionextracted with 5×200 mL EtOAc
  2. washThe combined EtOAc solution was washed with 200 mL 5% NaHCO3, 4×200 mL water, and 200 mL saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give crude product as a yellow oil
  6. customIt was purified on silica gel using 35-55% EtOAc in hexanes

Sources & evidence

ORD record
ord-b10dc7376fa34739b2e31bdb112136a6
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

Loading…