Lithium Hydroxide → HCID 10483151, compound

HRID 1613517Notes

Reaction equation

HRID 1613517 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]([S: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]([S: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 10483456HCID 10483456, compoundHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 10483151HCID 10483151, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

The compound of Example 27 (48 mg, 81.9 μmol) was added to 3.0 ml of 4:1 methanol/THF, and 0.17 ml of 1M lithium hydroxide was added. The mixture was allowed to react at room temperature for 2.75 hours. The reaction 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 (44 mg, 76.9 μmol, 94% yield). High resolution mass spectrum, m/e 527.2159 (calculated for C29H37NO4S2 (M-CO2), 527.2164).

Workup

  1. additionwas added
  2. customto react at room temperature for 2.75 hours
  3. washthe ethyl acetate layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-da66bd24511e4d638ef26996474a8609
Source dataset
uspto-grants-1993_03
Patent number
US05192782

Reaction notes

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