Potassium trimethylsilanolate → HCID 24954825, compound

HRID 1801608Notes

Reaction equation

HRID 1801608 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C@@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[CH3:17])=[CH:10][C:3]=1[O:4][CH2:5][C:6]([O:8]C)=[O:7].C[Si](C)(C)[O-].[K+]>C1COCC1>[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C@@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[CH3:17])=[CH:10][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 24954100HCID 24954100, compound

Product 1

HCID 24954825HCID 24954825, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-methyl 2-(2-chloro-5-((1-(3-chlorophenyl)ethylamino) methyl)phenoxy)acetate 100 (50 mg, 136 μmol) in 2 mL of dry THF, was added potassium trimethylsilanolate (17 mg, 136 μmol). The solution was stirred at ambient temperature for 2 h. The reaction was concentrated and the resulting crude material was purified with reverse phase preparatory HPLC. The desired fractions were combined and lyophilized to give (R)-2-(2-chloro-5-((1-(3-chlorophenyl)ethylamino)methyl)phenoxy)acetic acid 101 (35 mg, 73% yield) as a white solid and as the TFA salt. 1H NMR (400 MHz, d4-methanol) δ ppm 1.71 (d, J=6.85 Hz, 3H) 3.98 (d, J=13.30 Hz, 1H) 4.16 (d, J=13.11 Hz, 1H) 4.44 (m, 1H) 4.81 (s, 2H) 6.97-7.01 (m, 1H) 7.05-7.07 (m, 1H) 7.41-7.52 (m, 4H) 7.54-7.57 (s, 1H). Mass spectrum: calculated for C17H17Cl2NO3 354.2. found 355.3 (M++1).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe resulting crude material was purified with reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-35ff0dc9be9d4743bb20a7dcc329a9da
Source dataset
uspto-grants-2013_01
Patent number
US08349831B2

Reaction notes

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