Diazomethane → Methyl (2S,3S)-3-t-butoxycarbonylamino-2-hydroxy-5-methylhexanoate

HRID 464900Notes

Reaction equation

HRID 464900 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][CH:16]([CH3:18])[CH3:17])[C@H:10]([OH:14])[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH2:21])=[N-]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][CH:16]([CH3:18])[CH3:17])[C@H:10]([OH:14])[C:11]([O:13][CH3:21])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 2762291N-Boc-(2S,3S)-2-hydroxy-3-amino-5-methylhexanoic acid

Product 1

HCID 13420965Methyl (2S,3S)-3-t-butoxycarbonylamino-2-hydroxy-5-methylhexanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1.00 g (3.8 mmole) of (2S,3S)-3-(t-butoxycarbonyl)amino-2-hydroxy-5-methylhexaneoic acid prepared according to the method of R. L. Johnson [J. Med. Chem., 25, 605 (1982)] in 30 ml. of methanol was added, with stirring and ice-cooling, an ethereal solution of diazomethane. The mixture was stirred at room temperature for 1 hour. The solvent was removed by distillation, and the solid thus obtained was recrystallized from hexane, to afford 952 mg. of colourless needles, melting at 84°-85° C.; [α]22 -10.2° (C=1.26, methanol).

Workup

  1. temperatureice-cooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. customThe solvent was removed by distillation
  4. customthe solid thus obtained
  5. customwas recrystallized from hexane
  6. customto afford 952 mg

Sources & evidence

ORD record
ord-be12f9d54cb544d585073c170e84b1a0
Source dataset
uspto-grants-1985_10
Patent number
US04548926

Reaction notes

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