1,2-Dichloroethane → HCID 86679548, compound

HRID 1776595Notes

Reaction equation

HRID 1776595 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([S:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[CH:5][C:4]=1[O:16][S:17]([CH3:20])(=[O:19])=[O:18].C(Cl)CCl.[Cl:25][C:26]1[CH:27]=[N+:28]([O-:51])[CH:29]=[C:30]([Cl:50])[C:31]=1[CH2:32][C@@H:33]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH:42]([F:44])[F:43])=[C:37]([O:45][CH2:46][CH:47]2[CH2:49][CH2:48]2)[CH:36]=1)O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:25][C:26]1[CH:27]=[N+:28]([O-:51])[CH:29]=[C:30]([Cl:50])[C:31]=1[CH2:32][C@@H:33]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH:42]([F:44])[F:43])=[C:37]([O:45][CH2:46][CH:47]2[CH2:49][CH2:48]2)[CH:36]=1)[O:12][C:11](=[O:13])[CH2:10][S:9][C:7](=[O:8])[C:6]1[CH:14]=[CH:15][C:3]([O:2][CH3:1])=[C:4]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:5]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 71092687HCID 71092687, compoundHCID 86679547HCID 86679547, compound

Product 1

HCID 86679548HCID 86679548, compoundYield 23.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-methoxy-3-(methylsulfonyloxy)benzoylthio)acetic acid (0.150 g, 0.468 mmol) in dry DCM (12 ml), EDC (0.090 g, 0.468 mmol) and DMAP (0.057 g, 0.468 mmol) were added followed by (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (0.197 g, 0.468 mmol) and the reaction was stirred at RT for 48 hours. The mixture was partitioned between DCM and HCl 1N; the organic phase was washed with NaHCO3 sat. sol., and dried over Na2SO4. The solvent was removed and the crude was purified by preparative HPLC to afford (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(4-methoxy-3-(methylsulfonyloxy)benzoylthio)-acetoxy)ethyl)pyridine 1-oxide (0.080 g, 0.111 mmol, 23.64% yield, MS/ESI+ 722.38 [MH]+, [αD]=−34.72, c=0.5, DCM).

Workup

  1. customThe mixture was partitioned between DCM and HCl 1N
  2. washthe organic phase was washed with NaHCO3 sat. sol.
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed
  5. customthe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-d2158c0df4f74059bbb4dd59ccbf8b85
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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