Triethylamine → HCID 67902483, compound

HRID 232232Notes

Reaction equation

HRID 232232 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.Cl[C:19]1([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](=[O:28])[O:20]1.C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][O:15][N:14]([C:19]2([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)=[O:30])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21](=[O:28])[O:20]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 8471TriethylamineHCID 14181640HCID 14181640, compoundHCID 20030930HCID 20030930, compound

Product 1

HCID 67902483HCID 67902483, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 5 ml of dichloromethane were dissolved 236 mg of (4S)-4-benzyloxycarbonylamino-3-isoxazolidinone and 347 mg of Compound (98). To the solution was added, under ice-cooling, 0.14 ml of triethylamine, and the mixture was stirred for 30 minutes. The solvent was evaporated off. To the residue was added ethyl acetate, which was washed with water and an aqueous saline solution. The organic layer was dried, then the solvent was evaporated off. The residue was subjected to a column chromatography using Florisil, followed by elution with hexane--ethyl acetate (2:1→1:1) to give 350 mg of the subject Compound (99) as a pale yellow oily product.

Workup

  1. additionTo the solution was added, under ice-
  2. temperaturecooling
  3. customThe solvent was evaporated off
  4. additionTo the residue was added ethyl acetate, which
  5. washwas washed with water
  6. customThe organic layer was dried
  7. customthe solvent was evaporated off
  8. washfollowed by elution with hexane--ethyl acetate (2:1→1:1)

Sources & evidence

ORD record
ord-70a207bade0a42bea2dbf24e17429536
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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