Trimethylsilyldiazomethane → [3-Bromo-6,6-dimethyl-11-oxo-8-((2R,3R)-2,3,4-trihydroxy-butoxy)-6,11-dihydro-benzo[b]carbazol-5-yl]-acetic acid methyl ester

HRID 61842Notes

Reaction equation

HRID 61842 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:33])[C:8]4[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@@H:27]([OH:32])[C@H:28]([OH:31])[CH2:29][OH:30])=[CH:21][C:9]=4[C:10]([CH3:20])([CH3:19])[C:11]=3[N:12]2[CH2:15][C:16]([OH:18])=[O:17])=[CH:4][CH:3]=1.[CH3:34][Si](C=[N+]=[N-])(C)C>CO>[CH3:34][O:17][C:16](=[O:18])[CH2:15][N:12]1[C:11]2[C:10]([CH3:20])([CH3:19])[C:9]3[CH:21]=[C:22]([O:25][CH2:26][C@@H:27]([OH:32])[C@H:28]([OH:31])[CH2:29][OH:30])[CH:23]=[CH:24][C:8]=3[C:7](=[O:33])[C:6]=2[C:5]2[C:13]1=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=2

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 66834897HCID 66834897, compound

Product 1

HCID 70192943[3-Bromo-6,6-dimethyl-11-oxo-8-((2R,3R)-2,3,4-trihydroxy-butoxy)-6,11-dihydro-benzo[b]carbazol-5-yl]-acetic acid methyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[3-Bromo-6,6-dimethyl-11-oxo-8-((2R,3R)-2,3,4-trihydroxy-butoxy)-6,11-dihydro-benzo[b]carbazol-5-yl]-acetic acid (Compound T22-6, 15.0 mg, 29.0 μmol) was dissolved in methanol (0.30 mL), added with trimethylsilyldiazomethane (0.10 mL), and then stirred at room temperature for 1 hr. The residues obtained from the reaction solution after concentration under reduced pressure were purified by silica gel column chromatography (methylene chloride/methanol) to obtain the target compound (15.2 mg, 96%).

Workup

  1. customThe residues obtained from the reaction solution
  2. concentrationafter concentration under reduced pressure
  3. customwere purified by silica gel column chromatography (methylene chloride/methanol)

Sources & evidence

ORD record
ord-332e339f2fef408db6e7c70e740b5d43
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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