Lithium Hydroxide → HCID 25056270, compound

HRID 2101787Notes

Reaction equation

HRID 2101787 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([CH3:15])[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.Cl[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:33]([CH3:36])([CH3:35])[CH3:34])=[C:22]([C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=2[F:32])[CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Li+]>CS(C)=O>[CH3:36][C:33]([C:21]1[C:22]([C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=2[F:32])=[CH:23][C:18]([CH2:17][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C@@H:9]([CH3:15])[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=2)=[CH:19][CH:20]=1)([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 10796Cesium carbonateHCID 57672457HCID 57672457, compoundHCID 57801814HCID 57801814, compound

Product 1

HCID 25056270HCID 25056270, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A reaction mixture of (R)-ethyl 3-(4-hydroxyphenyl)-2-methylpropanoate (40.0 mg, 192 μmol), 5-(chloromethyl)-2-(1,1-dimethylethyl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl A (58.9 mg, 192 μmol) and cesium carbonate (125.1 mg, 384 μmol) in DMSO (1.0 mL) was stirred at room temperature for 16 hours. Lithium hydroxide (0.3 mL, 3.33 M in water) and DMSO (1.0 mL) were added, and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was purified by preparative HPLC (reverse phase) to give the title compound 26. 1H NMR (400 MHz, CD3CN) δ ppm 1.11 (d, J=6.65 Hz, 3H) 1.23 (s, 9H) 2.62-2.71 (m, 2H) 2.89 (s, 1H) 3.79 (s, 3H) 5.04 (s, 2H) 6.84-6.98 (m, 4H) 7.07-7.15 (m, 4H) 7.44 (dd, J=8.22, 1.96 Hz, 1H) 7.64 (d, J=8.22 Hz, 1H). MS ESI (neg.) m/e: 449.2 (M−H)+.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 16 hours
  2. customThe reaction mixture was purified by preparative HPLC (reverse phase)

Sources & evidence

ORD record
ord-fd9f923ab9564e2eb8d7b3c66c86a7c0
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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