Triethylamine → methyl 2-((S)-6-((2',6'-dimethyl-4'-(((S)-1-(methylsulfonyl)pyrrolidin-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 2280646Notes

Reaction equation

HRID 2280646 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][C@H:9]2[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:4]([CH3:14])[C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][C:23]2[CH:36]=[CH:35][C:26]3[C@H:27]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH2:28][O:29][C:25]=3[CH:24]=2)[CH:16]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39].C(N(CC)CC)C.C(OCC)(=O)C>ClCCl>[CH3:14][C:4]1[CH:5]=[C:6]([O:8][C@H:9]2[CH2:13][CH2:12][N:11]([S:38]([CH3:37])(=[O:40])=[O:39])[CH2:10]2)[CH:7]=[C:2]([CH3:1])[C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][C:23]2[CH:36]=[CH:35][C:26]3[C@H:27]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH2:28][O:29][C:25]=3[CH:24]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 89701736HCID 89701736, compound

Product 1

HCID 89701802methyl 2-((S)-6-((2',6'-dimethyl-4'-(((S)-1-(methylsulfonyl)pyrrolidin-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetateYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude methyl 2-((S)-6-((2′,6′-dimethyl-4′-((S)-pyrrolidin-3-yloxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 8a (45 mg, 0.09 mmol) was dissolved in 3 mL of dichloromethane, followed by addition of methanesulfonyl chloride (13 mg, 0.11 mmol) and triethylamine (18 mg, 0.18 mmol). The reaction solution was stirred for 2 hours. The resulting solution was added with 30 mL of ethyl acetate. The organic phase was washed with saturated sodium chloride solution (30 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by TLC with elution system A to obtain the title compound methyl 2-((S)-6-((2′,6′-dimethyl-4′-(((S)-1-(methylsulfonyl)pyrrolidin-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 8b (40 mg, yield 77.0%) as a colorless oil.

Workup

  1. washThe organic phase was washed with saturated sodium chloride solution (30 mL)
  2. dry with materialdried with anhydrous magnesium sulphate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by TLC with elution system

Sources & evidence

ORD record
ord-1e71528e689f4977a312e2cf1501a191
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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