1,4-Dioxane → HCID 86679538, compound

HRID 1776585Notes

Reaction equation

HRID 1776585 reaction equation
C(OC([O:8][C:9]1[CH:47]=[CH:46][C:45]([N:48]([CH2:53][CH:54]2[CH2:56][CH2:55]2)[S:49]([CH3:52])(=[O:51])=[O:50])=[CH:44][C:10]=1[C:11]([O:13][CH2:14][C:15]([O:17][C@H:18]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([F:38])[F:37])=[C:31]([O:39][CH2:40][CH:41]2[CH2:43][CH2:42]2)[CH:30]=1)[CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][N+:23]([O-:27])=[CH:22][C:21]=1[Cl:28])=[O:16])=[O:12])=O)(C)(C)C.O1CCOCC1>C(Cl)Cl.Cl>[Cl:28][C:21]1[CH:22]=[N+:23]([O-:27])[CH:24]=[C:25]([Cl:26])[C:20]=1[CH2:19][C@@H:18]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([F:37])[F:38])=[C:31]([O:39][CH2:40][CH:41]2[CH2:43][CH2:42]2)[CH:30]=1)[O:17][C:15](=[O:16])[CH2:14][O:13][C:11](=[O:12])[C:10]1[CH:44]=[C:45]([N:48]([CH2:53][CH:54]2[CH2:55][CH2:56]2)[S:49]([CH3:52])(=[O:51])=[O:50])[CH:46]=[CH:47][C:9]=1[OH:8]

Participants

5

Reactant 2

HCID 312751,4-Dioxane2×HCID 86679537HCID 86679537, compound

Product 1

HCID 86679538HCID 86679538, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-4-(2-(2-(2-(tert-butoxycarbonyloxy)-5-(N-(cyclopropyl-methyl)methylsulfonamido)benzoyloxy)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (0.326 g, 0.385 mmol) in DCM (15 ml), HCl 4M in dioxane (1 ml, 4.00 mmol) was added, and the mixture was stirred at RT overnight. Additional HCl 4M in dioxane (1 ml, 4.00 mmol) was added, and the mixture was stirred at the same temperature for 3 days. The solvent was removed and the crude was triturated with MeOH. The solid was collected by filtration and washed with ethyl ether. A further trituration with EtOAc was required to afford (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(5-(N-(cyclopropylmethyl)-methylsulfonamido)-2-hydroxybenzoyloxy)acetoxy)ethyl)pyridine 1-oxide as a white solid (0.160 g, 0.215 mmol, 55.7% yield, MS/ESI+ 745.19 [MH]+, [αD]=−36.29, c=0.49, DCM).

Workup

  1. stirringthe mixture was stirred at the same temperature for 3 days
  2. customThe solvent was removed
  3. customthe crude was triturated with MeOH
  4. filtrationThe solid was collected by filtration
  5. washwashed with ethyl ether

Sources & evidence

ORD record
ord-7f55c89d8e0245dfa2b516aa3dd82d6e
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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