Trifluoroacetic acid → (S)-Methyl 2-(6-((4'-(azetidin-3-yloxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 2,2,2-trifluoroacetate

HRID 2280661Notes

Reaction equation

HRID 2280661 reaction equation
[CH3:1][O:2][C:3](=[O:42])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH2:15][C:16]3[CH:17]=[C:18]([C:22]4[C:27]([CH3:28])=[CH:26][C:25]([O:29][CH:30]5[CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31]5)=[CH:24][C:23]=4[CH3:41])[CH:19]=[CH:20][CH:21]=3)=[CH:13][C:8]=2[O:7][CH2:6]1.[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46]>ClCCl>[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[NH:32]1[CH2:33][CH:30]([O:29][C:25]2[CH:24]=[C:23]([CH3:41])[C:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][O:14][C:12]4[CH:11]=[CH:10][C:9]5[C@H:5]([CH2:4][C:3]([O:2][CH3:1])=[O:42])[CH2:6][O:7][C:8]=5[CH:13]=4)[CH:17]=3)=[C:27]([CH3:28])[CH:26]=2)[CH2:31]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89701788(S)-tert-butyl 3-((3'-(((3-(2-methoxy-2-oxoethyl)-2,3-dihydrobenzofuran-6-yl)oxy)methyl)-2,6-dimethylbiphenyl-4-yl)oxy)azetidine-1-carboxylate

Product 1

HCID 131733506(S)-Methyl 2-(6-((4'-(azetidin-3-yloxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 2,2,2-trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 3-((3′-(((3-(2-methoxy-2-oxoethyl)-2,3-dihydrobenzofuran-6-yl)oxy)methyl)-2,6-dimethylbiphenyl-4-yl)oxy)azetidine-1-carboxylate 14b (100 mg, 0.17 mmol) was dissolved in 5 mL of dichloromethane, followed by addition of 1 mL of trifluoroacetic acid. The reaction solution was stirred for 2 hours. The resulting solution was concentrated under reduced pressure to obtain the crude title compound

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7f84f661426340dea2aeaa18723feb42
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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