Lithium Hydroxide → HCID 59337731, compound

HRID 2192230Notes

Reaction equation

HRID 2192230 reaction equation
[CH2:1]([N:6]1[CH2:11][CH2:10][C:9]2([C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[NH:26][C:27]([NH:29]C(=O)C3C=CC=CC=3)=[S:28])[CH2:12]2)[CH2:8][CH2:7]1)[C:2]([CH3:5])([CH3:4])[CH3:3].[Li+].[OH-]>C1COCC1.CO>[CH2:1]([N:6]1[CH2:7][CH2:8][C:9]2([C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[NH:26][C:27]([NH2:29])=[S:28])[CH2:12]2)[CH2:10][CH2:11]1)[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59337717HCID 59337717, compound

Product 1

HCID 59337731HCID 59337731, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 20g (138 mg, 0.27 mmol) and 1 N LiOH (0.5 mL) in THF/MeOH (2:1, 3 mL) was stirred at 50° C. for 2 h. The reaction was concentrated and the residue was extracted with EtOAc. The combined organic layers were dried over magnesium sulfate, concentrated and purified by flash chromatography (silica gel, 0-10% MeOH/DCM) to give 20h as yellow solid (83 mg). LC-MS m/z 409.0 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. extractionthe residue was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated
  5. custompurified by flash chromatography (silica gel, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-0921937da2294d538c416dc0e3b32afc
Source dataset
uspto-grants-2012_12
Patent number
US08329718B2

Reaction notes

Loading…