1,4-Dioxane → HCID 86679448, compound

HRID 1776500Notes

Reaction equation

HRID 1776500 reaction equation
C(OC([N:8]([CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[C:42]([O:48][CH3:49])[CH:41]=1)[CH2:9][C:10]([O:12][C@H:13]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:33])[F:32])=[C:26]([O:34][CH2:35][CH:36]2[CH2:38][CH2:37]2)[CH:25]=1)[CH2:14][C:15]1[C:20]([Cl:21])=[CH:19][N+:18]([O-:22])=[CH:17][C:16]=1[Cl:23])=[O:11])=O)(C)(C)C.O1CCOCC1>C(Cl)Cl.Cl>[ClH:21].[Cl:21][C:20]1[CH:19]=[N+:18]([O-:22])[CH:17]=[C:16]([Cl:23])[C:15]=1[CH2:14][C@@H:13]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:33])[F:32])=[C:26]([O:34][CH2:35][CH:36]2[CH2:37][CH2:38]2)[CH:25]=1)[O:12][C:10](=[O:11])[CH2:9][NH:8][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[C:42]([O:48][CH3:49])[CH:41]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 86679447HCID 86679447, compound

Product 1

HCID 86679448HCID 86679448, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-4-(2-(2-(tert-butoxycarbonyl(3,4-dimethoxybenzyl)-amino)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (258 mg, 0.355 mmol) in DCM (24 ml), HCl 4M in dioxane (1.2 ml, 4.80 mmol) was added drop wise, and the reaction was stirred at RT overnight. The volatiles were evaporated under vacuum and the residue was purified by trituration with diethylether affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(3,4-dimethoxybenzylamino) acetoxy)ethyl)pyridine 1-oxide hydrochloride as a beige solid (0.187 g, 0.282 mmol, 79% yield, MS/ESI+ 626.82 [MH]+, [αD]=−15.57, c=0.56, MeOH).

Workup

  1. customThe volatiles were evaporated under vacuum
  2. customthe residue was purified by trituration with diethylether

Sources & evidence

ORD record
ord-37b5ea75e9fe4a3da9c8ba80909fdd17
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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