1,4-Dioxane → HCID 71541989, compound

HRID 1776537Notes

Reaction equation

HRID 1776537 reaction equation
C(OC([N:8]([C:13]1[CH:14]=[C:15]([CH:49]=[CH:50][C:51]=1[O:52][CH3:53])[C:16]([O:18][CH2:19][C:20]([O:22][C@H:23]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH:41]([F:43])[F:42])=[C:36]([O:44][CH2:45][CH:46]2[CH2:48][CH2:47]2)[CH:35]=1)[CH2:24][C:25]1[C:30]([Cl:31])=[CH:29][N+:28]([O-:32])=[CH:27][C:26]=1[Cl:33])=[O:21])=[O:17])[S:9]([CH3:12])(=[O:11])=[O:10])=O)(C)(C)C.O1CCOCC1>C(Cl)Cl.Cl>[Cl:33][C:26]1[CH:27]=[N+:28]([O-:32])[CH:29]=[C:30]([Cl:31])[C:25]=1[CH2:24][C@@H:23]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH:41]([F:42])[F:43])=[C:36]([O:44][CH2:45][CH:46]2[CH2:47][CH2:48]2)[CH:35]=1)[O:22][C:20](=[O:21])[CH2:19][O:18][C:16](=[O:17])[C:15]1[CH:49]=[CH:50][C:51]([O:52][CH3:53])=[C:13]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:14]=1

Participants

5

Reactant 2

HCID 312751,4-Dioxane2×HCID 89455737HCID 89455737, compound

Product 1

HCID 71541989HCID 71541989, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-4-(2-(2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxybenzoyloxy)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)-phenyl)ethyl)-3,5-dichloropyridine 1-oxide (0.296 g, 0.367 mmol) in DCM (20 ml), HCl 4M in dioxane (0.919 ml, 3.67 mmol) was added, and the mixture was stirred at RT for 3 days. Additional HCl 4M in dioxane (1.838 ml, 7.34 mmol) was added over 2 days with stirring at the same temperature. The volatiles was removed under vacuum, and the crude was triturated with MeOH. The precipitate was collected by filtration and washed with Et2O to give (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(4-methoxy-3-(methylsulfonamido)benzoyloxy)-acetoxy)ethyl)pyridine 1-oxide as a white solid (0.215 g, 0.305 mmol, 83% yield, MS/ESI+ 705.25 [MH]+, [αD]=−28.15, c=0.53, DCM).

Workup

  1. stirringwith stirring at the same temperature
  2. customThe volatiles was removed under vacuum
  3. customthe crude was triturated with MeOH
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with Et2O

Sources & evidence

ORD record
ord-f4338507b038451e991b642c01cf59a7
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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