Hydrochloric Acid → HCID 86679524, compound

HRID 1776568Notes

Reaction equation

HRID 1776568 reaction equation
[C:1]([S:4][C:5]([CH3:45])([CH3:44])[CH:6]([NH:36]C(OC(C)(C)C)=O)[C:7]([O:9][C@H:10]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]([F:30])[F:29])=[C:23]([O:31][CH2:32][CH:33]2[CH2:35][CH2:34]2)[CH:22]=1)[CH2:11][C:12]1[C:17]([Cl:18])=[CH:16][N+:15]([O-:19])=[CH:14][C:13]=1[Cl:20])=[O:8])(=[O:3])[CH3:2].Cl.O1CCOCC1>C(Cl)Cl>[C:1]([S:4][C:5]([CH3:45])([CH3:44])[CH:6]([NH2:36])[C:7]([O:9][C@H:10]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]([F:30])[F:29])=[C:23]([O:31][CH2:32][CH:33]2[CH2:35][CH2:34]2)[CH:22]=1)[CH2:11][C:12]1[C:13]([Cl:20])=[CH:14][N+:15]([O-:19])=[CH:16][C:17]=1[Cl:18])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86679523HCID 86679523, compound

Product 1

HCID 86679524HCID 86679524, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-((2S)-2-(3-(acetylthio)-2-(tert-butoxycarbonylamino)-3-methylbutanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (118 mg, 0.170 mmol) was dissolved in DCM (1 ml). HCl 4N in dioxane (425 μl, 1.70 mmol) was added and the mixture stirred for 30 minutes at RT. The reaction mixture was diluted with DCM. The organic layer was washed with NaHCO3 sat. sol. (2×) and brine, dried over Na2SO4 and evaporated under vacuum. The crude product was purified by preparative reverse-phase HPLC to give 101 mg of the desired compound (quantitative yield).

Workup

  1. washThe organic layer was washed with NaHCO3 sat. sol. (2×) and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated under vacuum
  4. customThe crude product was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-4294ce39af424e1484cf65c0105eeecd
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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