1,2-Dichloroethane → HCID 86679580, compound

HRID 1776622Notes

Reaction equation

HRID 1776622 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[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].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([S:38]([O:41][CH2:42][C:43](O)=[O:44])(=[O:40])=[O:39])[CH:33]=[CH:34][C:35]=1[O:36][CH3:37].C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl.Cl>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[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][O:41][S:38]([C:32]1[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:30]([O:29][CH3:28])[CH:31]=1)(=[O:40])=[O:39]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 24262708HCID 24262708, compoundHCID 71092687HCID 71092687, compound

Product 1

HCID 86679580HCID 86679580, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (30 mg, 0.071 mmol), 2-(3,4-dimethoxyphenyl-sulfonyloxy)acetic acid (39.4 mg, 0.143 mmol), DMAP (8.72 mg, 0.071 mmol), and EDC (20.53 mg, 0.107 mmol) were dissolved in DCM (2 ml). The reaction was stirred at RT for 1.5 hours. The reaction mixture was diluted with HCl 1N and extracted with DCM. The organic phase was washed with HCl 1N, Na2CO3 sat and brine, dried over Na2SO4 and concentrated under vacuum. The crude product was triturated in EtOH to give (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(3,4-dimethoxyphenylsulfonyloxy)acetoxy)-ethyl)pyridine 1-oxide (30 mg, 0.044 mmol, 61.9% yield).

Workup

  1. extractionextracted with DCM
  2. washThe organic phase was washed with HCl 1N, Na2CO3
  3. dry with materialbrine, dried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe crude product was triturated in EtOH

Sources & evidence

ORD record
ord-bedc65ef7eb340c9a0feb8dcc4ee875c
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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