Methanol → HCID 9985465, compound

HRID 1461160Notes

Reaction equation

HRID 1461160 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:36][CH2:37][CH3:38])=[C:5]([CH:27]=[CH:28][C:29]=1[C:30](=O)[CH2:31][S:32][C:33]#[N:34])[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:23]=[CH:22][C:14]2[CH2:15][CH2:16]C(C([O-])=O)[O:18][C:13]=2[C:12]=1[CH2:24][CH2:25][CH3:26].CO.C[O-].[Na+].[CH2:44]([O:46]CC)C.O.CCCCCC.[C:56]([O:59][CH2:60]C)(=[O:58])[CH3:57]>>[CH3:1][O:2][C:3]1[C:4]([CH2:36][CH2:37][CH3:38])=[C:5]([CH:27]=[CH:28][C:29]=1[C:30]1[N:34]=[C:33]([O:46][CH3:44])[S:32][CH:31]=1)[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:23]=[CH:22][C:14]2[CH2:15][CH2:16][CH:57]([C:56]([O:59][CH3:60])=[O:58])[O:18][C:13]=2[C:12]=1[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 5

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 19981401HCID 19981401, compoundHCID 21226206Ethyl acetate hexaneHCID 21584184Diethylether water

Product 1

HCID 9985465HCID 9985465, compoundYield 39%

Procedure

The compound of Example 22 (20 mg, 35.9 μmol) was mixed with 2 mL of methanol and about 10 mg sodium methoxide, and the reaction mixture was held at room temperature for 30 min. The reaction mixture was poured into ethyl ether/water, and the ether layer was washed with brine, dried over sodium sulfate, and concentrated. Flash chromatography on silica gel using 20:1 to 10:1 to 5:1 hexane/ethyl acetate as eluant gave the product (24 mg, 42.1 μmol, 39% yield). High resolution mass spectrum, m/e 569.2438 (calculated for C31H39NO7S, 569.2447).

Workup

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

Sources & evidence

ORD record
ord-cea78c35fab74bb8a5c13facba4f9fc3
Source dataset
uspto-grants-1991_12
Patent number
US05073562

Reaction notes

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