Lithium Hydroxide → HCID 57672426, compound

HRID 2101809Notes

Reaction equation

HRID 2101809 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8](/[CH:15]=[CH:16]\[CH3:17])[C@H:9]([CH3:14])[C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.Cl[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:35]([CH3:38])([CH3:37])[CH3:36])=[C:24]([C:26]2[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=2[F:34])[CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Li+]>CS(C)=O>[CH3:38][C:35]([C:23]1[C:24]([C:26]2[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=2[F:34])=[CH:25][C:20]([CH2:19][O:1][C:2]2[CH:7]=[CH:6][C:5]([C@H:8](/[CH:15]=[CH:16]\[CH3:17])[C@H:9]([CH3:14])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=2)=[CH:21][CH:22]=1)([CH3:36])[CH3:37]

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 10796Cesium carbonateHCID 57672469HCID 57672469, compoundHCID 57801814HCID 57801814, compound

Product 1

HCID 57672426HCID 57672426, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A reaction mixture of (2S,3R,Z)-methyl 3-(4-hydroxyphenyl)-2-methylhex-4-enoate 41.3 (34.0 mg, 145 μmol), 5-(chloromethyl)-2-(1,1-dimethylethyl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl A (44.5 mg, 145 μmol) and cesium carbonate (94.5 mg, 290 μmol) in DMSO (1.0 mL) was stirred at room temperature for 16 hours. Lithium hydroxide (0.4 mL, 3.33M in water) and DMSO (1.5 mL) were added, and the resulting mixture was stirred at ambient temperature for 16 hours. The reaction mixture was purified by HPLC (reverse phase) to give the title compound 41. 1H NMR (500 MHz, CD3CN) δ ppm 1.17 (d, J=7.09 Hz, 3H) 1.23 (s, 9H) 2.76 (m, 1H) 3.78-3.82 (m, 4H) 5.04 (s, 2H) 5.53-5.57 (m, 1H) 6.85 (dd, J=5.87, 3.18 Hz, 1H) 6.90-6.98 (m, 3H) 7.07-7.12 (m, 2H) 7.18 (d, J=8.56 Hz, 2H) 7.44 (dd, J=8.31, 1.96 Hz, 1H) 7.64 (d, J=8.31 Hz, 1H). MS ESI (neg.) m/e: 489.2 (M−H)+.

Workup

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

Sources & evidence

ORD record
ord-7f726a39689548b58e43e525d9fc3a8b
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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