methyl (S)-2-(6-((4'-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate → (S)-methyl 2-(6-((2',6'-dimethyl-4'-(piperidin-4-yloxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 2280640Notes

Reaction equation

HRID 2280640 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([CH3:21])[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][O:29][C:30]4[CH:43]=[CH:42][C:33]5[C@H:34]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH2:35][O:36][C:32]=5[CH:31]=4)[CH:23]=3)=[C:17]([CH3:44])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[CH3:21][C:19]1[CH:20]=[C:15]([O:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:16]=[C:17]([CH3:44])[C:18]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][O:29][C:30]2[CH:43]=[CH:42][C:33]3[C@H:34]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH2:35][O:36][C:32]=3[CH:31]=2)[CH:23]=1

Participants

4

Reactant 1

HCID 89701758methyl (S)-2-(6-((4'-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 89701746(S)-methyl 2-(6-((2',6'-dimethyl-4'-(piperidin-4-yloxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetateYield 115%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl (S)-2-(6-((4′-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2′,6′-dimethyl-biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 3j (75 mg, 0.13 mmol) was dissolved in 15 mL hydrochloric acid in dioxane. The reaction solution was reacted for 1 hour. The resulting solution was concentrated under reduced pressure to obtain the crude title compound (S)-methyl 2-(6-((2′,6′-dimethyl-4′-(piperidin-4-yloxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 4a (75 mg), as a white solid which was directly used in the next step without further purification.

Workup

  1. customThe reaction solution was reacted for 1 hour
  2. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0b53a0e68b0345608581719b47f23629
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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