1,2-Dichloroethane → HCID 86641367, compound

HRID 885846Notes

Reaction equation

HRID 885846 reaction equation
[K+].[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:24])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([O-])=[O:22])=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:39][O:40][CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][O:42]1>C1COCC1.CN(C=O)C>[OH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:24])/[CH:11]=[CH:12]/[C:13]2[CH:14]=[CH:15][C:16](/[CH:19]=[CH:20]/[C:21]([NH:39][O:40][CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][O:42]3)=[O:22])=[CH:17][CH:18]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 67049447HCID 67049447, compound

Product 1

HCID 86641367HCID 86641367, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (E)-3-{4-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-phenyl}-acrylic acid potassium salt (1.39 g, 4.01 mmol), EDC (1.53 g, 8.03 mmol), HOBT (1.08 g, 8.03 mmol), TEA (1.11 ml, 8.03 mmol), NH2OTHP (939 mg, 8.03 mmol) in THF (20 ml) and DMF (20 ml) was stirred at room temperature overnight and then partitioned between water and AcOEt. The organic phase was washed with water, dried over Na2SO4 and evaporated in vacuo. The resulting solid was triturated with di-isopropylether and filtered to give 1.15 g of (E)-3-{4-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-phenyl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide.

Workup

  1. custompartitioned between water and AcOEt
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe resulting solid was triturated with di-isopropylether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ce26c025b47746ddb6b3e4eb6d076d24
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

Loading…