Water → (E)-ethyl 3-(4-(4-(N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)sulfamoyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate

HRID 45691Notes

Reaction equation

HRID 45691 reaction equation
Cl[S:2]([C:5]1[CH:27]=[CH:26][C:8]([O:9][C:10]2[C:15]([F:16])=[CH:14][C:13](/[CH:17]=[C:18](\[CH3:24])/[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12][C:11]=2[F:25])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[N:28]([CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][NH2:42])=[N+:29]=[N-:30].C(N(CC)CC)C.O>C(Cl)Cl>[N:28]([CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][NH:42][S:2]([C:5]1[CH:27]=[CH:26][C:8]([O:9][C:10]2[C:15]([F:16])=[CH:14][C:13](/[CH:17]=[C:18](\[CH3:24])/[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12][C:11]=2[F:25])=[CH:7][CH:6]=1)(=[O:4])=[O:3])=[N+:29]=[N-:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27352801-Amino-11-azido-3,6,9-trioxaundecaneHCID 86672338(E)-ethyl 3-(4-(4-(chlorosulfonyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate2×

Product 1

HCID 86672339(E)-ethyl 3-(4-(4-(N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)sulfamoyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylateYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (E)-ethyl 3-(4-(4-(chlorosulfonyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate (intermediate 41.3) (250 mg, 0.60 mmol) in DCM (3 mL) was added a solution of 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethanamine (157 mg, 0.72 mmol) and triethylamine (72 mg, 0.72 mmol) in DCM (2 mL). After 15 minutes, water (10 mL) was added and the reaction mixture was extracted with DCM (2×25 mL). The combined orgaic layers were washed with water (10 mL), brine (10 mL), dried (Na2SO4) and concentrated. The crude material was purified by flash chromatography on silica gel eluting with 50% EtOAc in DCM to give the title compound (169 mg).

Workup

  1. extractionthe reaction mixture was extracted with DCM (2×25 mL)
  2. washThe combined orgaic layers were washed with water (10 mL), brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography on silica gel eluting with 50% EtOAc in DCM

Sources & evidence

ORD record
ord-199563e105234712aa9009e8a9abcee2
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Reaction notes

Loading…