Dicyclohexylcarbodiimide → HCID 14167828, compound

HRID 655001Notes

Reaction equation

HRID 655001 reaction equation
[OH:1][CH:2]([CH:4]([CH:8]([NH2:16])[CH:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:10])[C:5](O)=[O:6])[CH3:3].C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[OH:1][CH:2]([CH:4]1[CH:8]([CH:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:10])[NH:16][C:5]1=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 17996247HCID 17996247, compound

Product 1

HCID 14167828HCID 14167828, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The thus obtained (2SR,3RS,4RS)-2-[1(SR)-hydroxyethyl]-3-amino-4-ethoxycarbonylpentanoic acid was suspended in dry acetonitrile (5 ml), and N,N'-dicyclohexylcarbodiimide (266 mg) was added thereto, and the resultant mixture was stirred at room temperature for 10 minutes and at 60° C. for 2 hours. After removal of the solvent under reduced pressure, ethyl acetate (5 ml) was added to the residue, followed by stirring at room temperature. The suspension was allowed to stand at 5° C. for 5 hours, and insoluble materials were collected by filtration and washed with cold ethyl acetate. The filtrate and the washings were combined together and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give (3SR,4SR)-3-[1(SR)-hydroxyethyl]-4-[1-(RS)-ethoxycarbonylethyl]-2-azetidinone.

Workup

  1. customAfter removal of the solvent under reduced pressure, ethyl acetate (5 ml)
  2. additionwas added to the residue
  3. filtrationinsoluble materials were collected by filtration
  4. washwashed with cold ethyl acetate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1fd19535df6e4f3ba9ef6edb5220045e
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

Loading…