Carbon Dioxide → HCID 24851762, compound

HRID 1009888Notes

Reaction equation

HRID 1009888 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][NH:22][C:23]([NH:25][C:26]([CH3:33])([CH3:32])[CH2:27][O:28]C(=O)C)=[O:24])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[C@@H:34]1[O:51][C@H:50]([CH2:52][O:53]C(=O)C)[C@@H:45]([O:46]C(=O)C)[C@H:40]([O:41]C(=O)C)[C@H:35]1[O:36]C(=O)C)(=O)C.C[O-].[Na+].C(=O)=O>CO>[OH:28][CH2:27][C:26]([NH:25][C:23]([NH:22][CH2:21][CH2:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C:8]2[C:9]([CH3:11])=[CH:10][C:5]([OH:4])=[C:6]([C@@H:34]3[O:51][C@H:50]([CH2:52][OH:53])[C@@H:45]([OH:46])[C@H:40]([OH:41])[C@H:35]3[OH:36])[CH:7]=2)=[CH:14][CH:15]=1)=[O:24])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 10942334Sodium MethoxideHCID 67304712HCID 67304712, compound

Product 1

HCID 24851762HCID 24851762, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a methanol solution (1 mL) of (1S)-1-[2-(acetoxy)-5-[4-[3-[[[[2-(acetoxy)-1,1-dimethylethyl)amino]carbonyl]amino]propyl]benzyl]-4-methylphenyl]-1,5-anhydro-2,3,4,6-tetra-O-acetyl-D-glucitol (70 mg) was added sodium methoxide (a 1 M methanol solution, 0.5 mL, 0.5 mmol), and the mixture was stirred for an hour at room temperature. To this reaction solution was added dry ice, and the solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (chloroform:methanol=5:1) to obtain the title compound (35 mg, 31%, 3 steps) as a colorless oily compound. NMR data and MS data of the compound are shown in Table 1.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThus obtained residue was purified with silica gel column chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-e2a35d09547140e2a36c54fdd5159b9e
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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