Diisopropylethylamine → HCID 67902445, compound

HRID 232203Notes

Reaction equation

HRID 232203 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:16][O:15][NH:14][C:13]1=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:28]1([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=2)=[O:35])[CH2:32][CH2:31][C:30](=[O:33])[O:29]1>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:16][O:15][N:14]([C:28]2([C:34]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=3)=[O:35])[CH2:32][CH2:31][C:30](=[O:33])[O:29]2)[C:13]1=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 14049831HCID 14049831, compoundHCID 14181639HCID 14181639, compound

Product 1

HCID 67902445HCID 67902445, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 4 ml of dichloromethane was dissolved 60 mg of (4R)-4-benzyloxycarbonylamino-3-isoxazolidinone. To the solution were added under ice-cooling 0.08 ml of diisopropyl ethylamine and 90 mg of the Compound (15) obtained in Example 15. The mixture was stirred for 15 minutes under ice-cooling, followed by stirring at room temperature for 30 minutes. The reaction solution was washed with water, which was dried (Na2SO4), then the solvent was evaporated off. The residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (1:1) to give 71 mg of the subject Compound (8) as colorless foamy product. The IR and NMR spectra of this product were in agreement with those of the Compound (8) obtained in Example 8.

Workup

  1. additionTo the solution were added under ice-
  2. temperaturecooling
  3. stirringby stirring at room temperature for 30 minutes
  4. washThe reaction solution was washed with water, which
  5. dry with materialwas dried (Na2SO4)
  6. customthe solvent was evaporated off
  7. washfollowed by elution with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-3ac6b1211123457289d1d38d4b568b62
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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