Triethylamine → HCID 67902341, compound

HRID 232216Notes

Reaction equation

HRID 232216 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.Cl[C:26]1([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])[CH2:30][CH:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:28](=[O:37])[O:27]1>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][O:15][N:14]([C:26]2([C:38]([O:40][CH2:41][C:42]3[CH:43]=[CH:44][C:45]([N+:48]([O-:50])=[O:49])=[CH:46][CH:47]=3)=[O:39])[CH2:30][CH:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:28](=[O:37])[O:27]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 20030906HCID 20030906, compound

Product 1

HCID 67902341HCID 67902341, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Production of Compound(64): In 6 ml of dichloromethane was suspended 280 mg of (4S)-4-benzyloxycarbonylamino-3-isoxazolidinone. To the suspension were added, under ice-cooling and stirring, 0.36 ml of triethylamine and 490 mg of the Compound (63) obtained in Example 63 dissolved in 1 ml of dichloromethane. The reaction was solution stirred at room temperature for 30 minutes, which was washed with water and dried (MgSO4). The solvent was evaporated off, and the residue was chromatographed on silica gel, followed by elution with hexane-ethylacetate (3:1) to give 470 mg of the subject Compound (64) as colorless oily product. The IR and NMR spectra of this product were in agreement with those of the Compound (64) obtained in Example 64.

Workup

  1. additionTo the suspension were added, under ice-
  2. temperaturecooling
  3. stirringstirred at room temperature for 30 minutes
  4. washwhich was washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated off
  7. customthe residue was chromatographed on silica gel
  8. washfollowed by elution with hexane-ethylacetate (3:1)

Sources & evidence

ORD record
ord-802f197d391741119935f4f88e58b2ac
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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