Lithium Hydroxide → HCID 11756030, compound

HRID 1613508Notes

Reaction equation

HRID 1613508 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:36][CH2:37][CH3:38])=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]1[N:32]=[CH:33][O:34][CH:35]=1)[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]2[CH2:15][CH2:16][CH:17]([C:19]([O:21]C)=[O:20])[O:18][C:13]=2[C:12]=1[CH2:25][CH2:26][CH3:27].[OH-].[Li+].Cl.C(OCC)(=O)C>CO.C1COCC1>[CH3:1][O:2][C:3]1[C:4]([CH2:36][CH2:37][CH3:38])=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]1[N:32]=[CH:33][O:34][CH:35]=1)[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]2[CH2:15][CH2:16][CH:17]([C:19]([OH:21])=[O:20])[O:18][C:13]=2[C:12]=1[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 3939Lithium Hydroxide2×HCID 10029751HCID 10029751, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 11756030HCID 11756030, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The compound of Example 4 (25 mg, 47.7 μmol) along with 1.0 ml of 4:1 methanol/THF, and 0.09 ml of 1N lithium hydroxide were stirred at 0° C. for thirty minutes. An additional 0.09 ml of 1N lithium hydroxide was added and the reaction mixture was stirred at room temperature for 45 minutes. The reaction mixture was poured into 0.5N hydrochloric acid/ethyl acetate. The ethyl acetate layer was washed with brine, dried over sodium sulfate, and concentrated under vacuum to give the product; melting point 136-139° C. High resolution mass spectrum m/e 510.2471 (calculated for C29H36NO7 (M+H), 510.2492).

Workup

  1. washThe ethyl acetate layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customto give the product

Sources & evidence

ORD record
ord-ba11233e1a61400d8bb3d58b4ceb9ef9
Source dataset
uspto-grants-1993_03
Patent number
US05192782

Reaction notes

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