Lithium Hydroxide → HCID 57672496, compound

HRID 2101763Notes

Reaction equation

HRID 2101763 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:18]([CH3:21])([CH3:20])[CH3:19])=[C:7]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[F:17])[CH:8]=1.[OH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH:30]([CH3:36])[C:31]([O:33]CC)=[O:32])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Li+]>CN(C=O)C.O>[F:17][C:10]1[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:9]=1[C:7]1[CH:8]=[C:3]([CH:4]=[CH:5][C:6]=1[C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:2][O:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][CH:30]([CH3:36])[C:31]([OH:33])=[O:32])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 10796Cesium carbonateHCID 20748401Ethyl 3-(4-hydroxyphenyl)-2-methylpropanoateHCID 57801814HCID 57801814, compound

Product 1

HCID 57672496HCID 57672496, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The reaction mixture of compound A (30.0 mg, 97.8 μmol), compound 12.3 (22.4 mg, 108 μmol) and cesium carbonate (38.2 mg, 117 μmol) in DMF (1.0 mL) was stirred at room temperature overnight. The resulting reaction mixture was treated with lithium hydroxide (23.4 mg, 978 μmol) in water (0.5 mL), and stirred at room temperature for 5 hours. The reaction mixture was purified by reverse phase preparative HPLC to give the title compound. MS ESI (neg.) m/e: 449 (M−H). 1H NMR (CD3CN) δ 7.61(d, 1H), 7.41(d, 1H), 7.11(d, 2H), 7.06(m, 2H), 6.93(m, 1H), 6.89(d, 2H), 6.81(d, 1H), 5.02(s, 2H), 3.77 (s, 3H), 2.86(dd, 1H), 2.63(m, 2H), 1.21(s, 9H), 1.09(d, 3H).

Workup

  1. customThe resulting reaction mixture
  2. stirringstirred at room temperature for 5 hours
  3. customThe reaction mixture was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-ef26f280882d4e66b14659ebd7c7d003
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

Loading…