1,2-Dichloroethane → HCID 86679417, compound

HRID 1776460Notes

Reaction equation

HRID 1776460 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[OH:10].C(Cl)CCl.[C:32]1([S:38]([CH2:41][CH2:42][C:43](O)=[O:44])(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[O:10][C:43](=[O:44])[CH2:42][CH2:41][S:38]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)(=[O:40])=[O:39]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 5552523-(Phenylsulfonyl)propanoic acidHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide

Product 1

HCID 86679417HCID 86679417, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

((S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide) (150 mg, 0.357 mmol), EDC (103 mg, 0.535 mmol), 3-(phenylsulfonyl)propanoic acid (84 mg, 0.393 mmol), and DMAP (65.4 mg, 0.535 mmol) in DCM (30 ml) were stirred at RT for 4 hours. The reaction mixture was washed with HCl 1N (2×) and NaHCO3 sat. sol. (2×); the organic layer was dried over Na2SO4 and evaporated to dryness. The residue was purified by trituration with iPr2O (10 ml). Further triturations with petroleum ether (15 ml) and Et2O (20 ml) were performed to afford (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3-(phenylsulfonyl)propanoyloxy)ethyl)pyridine

Workup

  1. washThe reaction mixture was washed with HCl 1N (2×) and NaHCO3 sat. sol. (2×)
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customevaporated to dryness
  4. customThe residue was purified by trituration with iPr2O (10 ml)

Sources & evidence

ORD record
ord-a613b419924f4df7b005d8d034997cc7
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…