Lithium Hydroxide → HCID 10347709, compound

HRID 1461162Notes

Reaction equation

HRID 1461162 reaction equation
[S:1]=[C:2]1[NH:6][C:5]([C:7]2[CH:34]=[CH:33][C:10]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]3[CH:29]=[CH:28][C:19]4[CH2:20][CH2:21][CH:22]([C:24]([O:26]C)=[O:25])[O:23][C:18]=4[C:17]=3[CH2:30][CH2:31][CH3:32])=[C:9]([CH2:35][CH2:36][CH3:37])[C:8]=2[O:38][CH3:39])=[CH:4][S:3]1.CO.C1COCC1.[OH-].[Li+]>C(OCC)(=O)C.O>[S:1]=[C:2]1[NH:6][C:5]([C:7]2[CH:34]=[CH:33][C:10]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]3[CH:29]=[CH:28][C:19]4[CH2:20][CH2:21][CH:22]([C:24]([OH:26])=[O:25])[O:23][C:18]=4[C:17]=3[CH2:30][CH2:31][CH3:32])=[C:9]([CH2:35][CH2:36][CH3:37])[C:8]=2[O:38][CH3:39])=[CH:4][S:3]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 10483150HCID 10483150, compoundHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 10347709HCID 10347709, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

The compound of Example 25 (47 mg, 82.2 μmol) was added to 2.5 ml of 4:1 methanol/THF, and 0.2 ml of 1 N lithium hydroxide was added. The mixture was allowed to react at room temperature for 2.5 hours. The reaction mixture was poured into ethyl acetate/water and the ethyl acetate was washed with brine, dried over sodium sulfate and concentrated. Flash chromatography of the residue of silica gel using 7:1 to 5:1 hexane/ethyl acetate (1% acetic acid) as eluant gave the product, melting point 149- 51° C., (44 mg, 79 μmol, 96% yield). High resolution mass spectrum, m/e 557.1895 (calculated for C29H5NO6S2, 557.1906).

Workup

  1. additionwas added
  2. customto react at room temperature for 2.5 hours
  3. washthe ethyl acetate was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customFlash chromatography of the residue of silica gel using 7:1 to 5:1 hexane/ethyl acetate (1% acetic acid) as eluant gave the product, melting point 149- 51° C., (44 mg, 79 μmol, 96% yield)

Sources & evidence

ORD record
ord-8b1d66d9bb4e4045a45339e692c97207
Source dataset
uspto-grants-1991_12
Patent number
US05073562

Reaction notes

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