Ethyl Acetate → HCID 67902350, compound

HRID 232226Notes

Reaction equation

HRID 232226 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.[CH3:18][O:19][CH2:20][CH:21]([C:38]([O-:40])=[O:39])[CH2:22][C:23](=O)[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:25].C1CCC(N=C=NC2CCCCC2)CC1.C(OCC)(=O)C>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][O:15][N:14]([C:23]2([C:24]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=3)=[O:25])[CH2:22][CH:21]([CH2:20][O:19][CH3:18])[C:38](=[O:39])[O:40]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 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 14181640HCID 14181640, compoundHCID 679023451-(4-Nitrobenzyl) 4-methoxymethyl-2-oxoglutarate

Product 1

HCID 67902350HCID 67902350, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 2 ml of dichloromethane were dissolved 121 mg of (4S)-4-benzyloxycarbonylamino-3-isoxazolidinone and 200 mg of the Compound (78) obtained in Example 78. To the solution was added a solution of 137 mg of DCC in 1 ml of dichloromethane. The solution was stirred at room temperature for 2 hours. To the reaction solution was added ethyl acetate. The crystals which separated out were filtered off, and the filtrate was washed with water and dried (MgSO4). The solvent was evaporated off, and the residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (2:1) to give 216 mg of the subject Compound (80) as a pale yellow oily product.

Workup

  1. customThe crystals which separated out
  2. filtrationwere filtered off
  3. washthe filtrate was washed with water
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated off
  6. washfollowed by elution with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-c38b6ae638b3488c8958c912d8f6921a
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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