Triethylamine → HCID 67902542, compound

HRID 232223Notes

Reaction equation

HRID 232223 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(CC)CC)C.[CH2:25]([CH:32]1[C:36](=[O:37])[O:35][C:34](Cl)([C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=2)=[O:39])[CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(OCC)(=O)C>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][O:15][N:14]([C:34]2([C:38]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=3)=[O:39])[CH2:33][CH:32]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:36](=[O:37])[O:35]2)[C:13]1=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 14181640HCID 14181640, compoundHCID 20030908HCID 20030908, compound

Product 1

HCID 67902542HCID 67902542, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 1 ml of dichloromethane were dissolved 55 mg of (4S)-4-benzyloxycarbonylamino-3-isoxazolidinone and 0.07 ml of triethylamine. To the solution was added, under ice-cooling while stirring, 100 mg of the Compound (74) obtained in Example 74. The reaction solution was stirred at room temperature for 30 minutes, to which was added 25 ml of ethyl acetate. The mixture was washed with water, an aqueous solution of sodium hydrogen carbonate and water, successively, which was then dried (MgSO4), followed by evaporating off the solvent. The residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (2:1) to give 70 mg of the subject Compound (75) as a pale yellow oily product. The IR and NMR spectra are in agreement with those of the Compound (75) obtained in Example 75.

Workup

  1. additionTo the solution was added, under ice-
  2. temperaturecooling
  3. stirringThe reaction solution was stirred at room temperature for 30 minutes, to which
  4. washThe mixture was washed with water
  5. dry with materialan aqueous solution of sodium hydrogen carbonate and water, successively, which was then dried (MgSO4)
  6. customby evaporating off the solvent
  7. washfollowed by elution with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-30a9b8597b06434fb6d29c4f02e83fa9
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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