Lithium Hydroxide → HCID 42608568, compound

HRID 2101811Notes

Reaction equation

HRID 2101811 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C@H:28]([CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH2:29][C:30]([O:32]C)=[O:31])=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[OH-].[Li+]>CO>[CH3:4][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([C@H:28]([CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH2:29][C:30]([OH:32])=[O:31])=[CH:26][CH:27]=2)=[CH:7][CH:6]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57672463HCID 57672463, compound

Product 1

HCID 42608568HCID 42608568, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction mixture of 43.2 (32.0 mg, 61 μmol) and lithium hydroxide (0.2 mL, 3.33M in water) in MeOH (1.0 mL) was stirred at ambient temperature for 16 hours. The reaction mixture was purified by HPLC (reverse phase) to give the title compound 43. 1H NMR (400 MHz, CD3CN) δ ppm 1.16 (s, 9H) 1.19-1.36 (m, 1H) 1.45-1.67 (m, 1H) 2.45 (d, J=8.61 Hz, 1H) 2.53 (d, J=6.65 Hz, 1H) 3.14 (s, 3H) 3.20 (t, J=6.46 Hz, 2H) 3.72 (s, 3H) 4.97 (s, 2H) 6.77 (dd, J=6.26, 3.13 Hz, 1H) 6.83-6.91 (m, 3H) 6.99-7.10 (m, 4H) 7.37 (dd, J=8.22, 1.96 Hz, 1H) 7.57 (d, J=8.22 Hz, 1H). MS ESI (neg.) m/e: 507.2 (M−H)+.

Workup

  1. customThe reaction mixture was purified by HPLC (reverse phase)

Sources & evidence

ORD record
ord-6823a2776c024f27b05f0787cd3d1fbc
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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