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

HRID 255617Notes

Reaction equation

HRID 255617 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH:10]([OH:14])[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[N+](=[CH2:23])=[N-]>C(OCC)C>[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][CH3:23])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 9550DiazomethaneHCID 13848631(2RS,3S)-3-tert-butyloxycarbonylamino-2-hydroxy-5-methylhexanoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.00 g (3.8 mmole) of 3(S)-t-butoxycarbonylamino-2-hydroxy-5-methylhexanoic acid prepared by the method of R. L. Johnson [J. Med. Chem., 25, 605 (1982)] in 30 ml, of methanol was stirred, whilst cooling with ice, and then a diethyl ether solution of diazomethane was added and the mixture was stirred at room temperature for 1 hour. The solvent was then distilled off and the resulting solid was recrystallized from hexane to give 952 mg of the title product as colorless needles, melting at 84°-85° C.; [α]25 -10.2° (C=1.26, methanol).

Workup

  1. temperaturewhilst cooling with ice
  2. distillationThe solvent was then distilled off
  3. customthe resulting solid was recrystallized from hexane

Sources & evidence

ORD record
ord-f1602008bb59499aa40402308358b05b
Source dataset
uspto-grants-1987_10
Patent number
US04698329

Reaction notes

Loading…