Trimethylsilyldiazomethane → HCID 11196284, compound

HRID 351374Notes

Reaction equation

HRID 351374 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si](C=[N+]=[N-])(C)(C)[CH3:19]>C(Cl)Cl.CO>[CH3:19][O:11][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:14][CH2:15][CH2:16][OH:17]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 11368613BOC-L-6-HYDROXYNORLEUCINE

Product 1

HCID 11196284HCID 11196284, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-tert-butoxycarbonylamino-6-hydroxy-hexanoic acid (1 g, 6 mmol) in 30 mL of CH2Cl2 and 5 mL of MeOH at rt was slowly added TMSCHN2 (10 mL), and the reaction mixture was left with stirring for 1 h. The solvent was remove under reduced pressure, and the resulting residue was diluted with water and EtOAc. The organic layer was separated, dried over Na2SO4, and concentrated to afford an oil (S)-2-tert-butoxycarbonylamino-6-hydroxy-hexanoic acid methyl ester. MS [M+H]+ 262.

Workup

  1. customat rt
  2. waitthe reaction mixture was left
  3. customThe solvent was remove under reduced pressure
  4. additionthe resulting residue was diluted with water and EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-128cfb126ae94b39ad97e56876a386e2
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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