HCID 89455815, compound → HCID 86679563, compound

HRID 1776603Notes

Reaction equation

HRID 1776603 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]([S: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>C(Cl)Cl.Cl.O1CCOCC1>[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][S: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 1

HCID 89455815HCID 89455815, compound

Product 1

HCID 86679563HCID 86679563, compoundYield 58.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-4-(2-(2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxybenzoylthio)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)-phenyl)ethyl)-3,5-dichloropyridine 1-oxide (0.082 g, 0.100 mmol) in DCM (4 ml), HCl 4M in dioxane was added, and the reaction was stirred at RT for 3 days. The volatiles were removed under vacuum, and the residue was purified by chromatography on silica gel column (DCM:MeOH=95:5) to afford (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(4-methoxy-3-(methylsulfonamido)benzoylthio)acetoxy)ethyl)pyridine 1-oxide (0.042 g, 0.058 mmol, 58.3% yield, MS/ESI+ 721.32 [MH]+, [αD]=−31.40, c=0.5, MeOH).

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe residue was purified by chromatography on silica gel column (DCM:MeOH=95:5)

Sources & evidence

ORD record
ord-752c3b0e6d2945e89a11055bcdbc1c23
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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