Sodium Methoxide → HCID 23581843, compound

HRID 1009892Notes

Reaction equation

HRID 1009892 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[C:24]1[CH:29]=[C:28]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][NH:39][C:40]([NH:42][C:43]([CH2:48][OH:49])([CH2:46][OH:47])[CH2:44][OH:45])=[O:41])=[CH:33][CH:32]=2)[C:27]([CH3:50])=[CH:26][C:25]=1[O:51]C(=O)C)(=O)C.C[O-].[Na+]>CO>[OH:47][CH2:46][C:43]([NH:42][C:40]([NH:39][CH2:38][CH2:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][C:28]2[C:27]([CH3:50])=[CH:26][C:25]([OH:51])=[C:24]([C@@H:6]3[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]3[OH:4])[CH:29]=2)=[CH:32][CH:33]=1)=[O:41])([CH2:48][OH:49])[CH2:44][OH:45]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67304415HCID 67304415, compound

Product 1

HCID 23581843HCID 23581843, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a methanol solution (600 μL) of (1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-[2-acetoxy-5-[4-[2-[[[[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]amino]carbonyl]amino]ethyl]benzyl]-4-methylphenyl]-D-glucitol (7.9 mg, 0.0104 mmol) was added a 2.5 wt. % methanol solution of sodium methoxide (34 μL, 0.015 mmol), and the mixture was stirred for an hour at room temperature. The solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (methanol) to obtain the title compound (3.0 mg, 52%) as a colorless amorphous compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThus obtained residue was purified with silica gel column chromatography (methanol)

Sources & evidence

ORD record
ord-700cb33b487a455fb3ee3e5402d6d8a5
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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