1,2-Dichloroethane → HCID 89455720, compound

HRID 1776659Notes

Reaction equation

HRID 1776659 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].[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33]([O:35][CH2:36][C:37](O)=[O:38])=[O:34].C(Cl)CCl>CN(C1C=CN=CC=1)C.C(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:37](=[O:38])[CH2:36][O:35][C:33]([C:29]1[S:28][CH:32]=[CH:31][CH:30]=1)=[O:34]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxideHCID 86679605HCID 86679605, compound

Product 1

HCID 89455720HCID 89455720, compoundYield 110.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (150 mg, 0.357 mmol), 2-(thiophene-2-carbonyloxy)acetic acid (80 mg, 0.428 mmol), EDC (205 mg, 1.071 mmol), and DMAP (43.6 mg, 0.357 mmol) were dissolved in DCM (15 ml), and the solution was stirred at room temperature overnight. The solution was diluted with DCM, washed with 1N HCl and 5% NaHCO3, then with brine. The organic phase was dried over Na2SO4, and the solvent was evaporated. The crude so obtained (233 mg of a pale yellow solid) was triturated with MeOH and sonicated; the fine solid so obtained was filtered and dried in vacuum oven overnight. The desired product was obtained as a white powder (133 mg, 0.226 mmol, 63.3% yield, LC-MS/ESI+ 588.04 [MH]+, [αD]=−24.78, c=0.51, CHCl3).

Workup

  1. washwashed with 1N HCl and 5% NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-54e9b57e67df4d08850c16c964cbf254
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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