Dicyclohexylcarbodiimide → HCID 67902445, compound

HRID 232193Notes

Reaction equation

HRID 232193 reaction equation
O=[C:2]([CH2:16][CH2:17][C:18]([O-:20])=[O:19])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)=[O:4].ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1.[CH2:46]([O:53][C:54]([NH:56][C@@H:57]1[CH2:61][O:60][NH:59][C:58]1=[O:62])=[O:55])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>ClCCl>[CH2:46]([O:53][C:54]([NH:56][C@@H:57]1[CH2:61][O:60][N:59]([C:2]2([C:3]([O:5][CH2:6][C:7]3[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=3)=[O:4])[CH2:16][CH2:17][C:18](=[O:19])[O:20]2)[C:58]1=[O:62])=[O:55])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 14181639HCID 14181639, compoundHCID 221664155-[(4-Nitrophenyl)methoxy]-4,5-dioxopentanoate

Product 1

HCID 67902445HCID 67902445, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 3 ml of dichloromethane were dissolved 85 mg of the Compound (1) obtained in Example 1 and 41 mg of 1-hydroxybenzotriazole (HOBT). To the solution was added 62 mg of DCC, and the mixture was stirred at room temperature for 30 minutes, to which was added 60 mg of (4R)-4-benzyloxycarbonylamino-3-isoxazolidinone, prepared by the method described in Journal of Medicinal Chemistry, 13 1013 (1970), followed by stirring at room temperature for 30 minutes. The insolubles which separated out were filtered off and washed with dichloromethane. The filtrate and the washing were combined and concentrated. The concentrate was dissolved in ethyl acetate. The solution was washed with an aqueous solution of sodium hydrogen carbonate and a saturated saline, successively, which was then dried (Na2SO4). The solvent was evaporated off under reduced pressure, and the residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (1:1) to give 96 mg of the subject compound (8) as colorless foamy substance.

Workup

  1. customprepared by the method
  2. stirringby stirring at room temperature for 30 minutes
  3. customThe insolubles which separated out
  4. filtrationwere filtered off
  5. washwashed with dichloromethane
  6. concentrationconcentrated
  7. dissolutionThe concentrate was dissolved in ethyl acetate
  8. washThe solution was washed with an aqueous solution of sodium hydrogen carbonate
  9. dry with materiala saturated saline, successively, which was then dried (Na2SO4)
  10. customThe solvent was evaporated off under reduced pressure
  11. washfollowed by elution with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-96f3f44a44ac4db781f05275bf97cf67
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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