Lithium Hydroxide → HCID 10007005, compound

HRID 1461158Notes

Reaction equation

HRID 1461158 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:36][CH:37]=[CH2:38])=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]1[N:32]=[CH:33][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>CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:4]([CH2:36][CH:37]=[CH2:38])=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]1[N:32]=[CH:33][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

6

Reactant 4

HCID 3939Lithium HydroxideHCID 10075893HCID 10075893, compoundHCID 21899815MeOH tetrahydrofuranHCID 22728543Water ethylacetate

Product 1

HCID 10007005HCID 10007005, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The compound of Example 16 (22 mg, 40.9 μmol), 1 mL 4:1 methanol/THF, and 100 mL 1 N lithium hydroxide were stirred at room temperature for 2.75 hours. The mixture was poured into ethyl acetate/water, and the ethyl acetate layer was washed with brine, dried over sodium sulfate and concentrated. Flash chromatography on silica gel using 5:1 hexane/ethyl acetate (1% acetic acid) provided the product (20 mg, 38.1 μmol, 93% yield). High resolution mass spectrum, m/e 479.2114 (calculated for C28H35NO4S (M-CO2), 479.2130).

Workup

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

Sources & evidence

ORD record
ord-702ed5d9368e4dc5b8d5d61b35d97466
Source dataset
uspto-grants-1991_12
Patent number
US05073562

Reaction notes

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