Lithium Hydroxide → HCID 9985159, compound

HRID 1461161Notes

Reaction equation

HRID 1461161 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:38][CH2:39][CH3:40])=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]1[N:32]=[C:33]([O:36][CH3:37])[S: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].CO.C1COCC1.[OH-].[Li+]>C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[C:4]([CH2:38][CH2:39][CH3:40])=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]1[N:32]=[C:33]([O:36][CH3:37])[S: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 HydroxideHCID 9985465HCID 9985465, compoundHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 9985159HCID 9985159, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

The compound of Example 23 (20 mg, 35.1 μmol) was added to 2 mL of 4:1 methanol/THF and 0.08 mL of 1 N lithium hydroxide, and the reaction was allowed to proceed at room temperature for 2.75 hr. The mixture was poured into ethyl acetate/water, and the ethyl acetate layer was washed with brine, dried over sodium sulfate, and concentrated to give the product (19 mg, 34.1 μmol, 97% yield).

Workup

  1. washthe ethyl acetate layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e1e60225a36e4ca5abb6f0f84f9f7b87
Source dataset
uspto-grants-1991_12
Patent number
US05073562

Reaction notes

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