Ethyl Acetate → HCID 67902542, compound

HRID 232222Notes

Reaction equation

HRID 232222 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.[CH2:18]([CH:25]([C:42]([O-])=[O:43])[CH2:26][C:27](=[O:41])[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:29])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.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:27]2([C:28]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=3)=[O:29])[CH2:26][CH:25]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:42](=[O:43])[O:41]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 67902300HCID 67902300, compound

Product 1

HCID 67902542HCID 67902542, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 6 ml of dichloromethane were dissolved 286 mg of (4S)-4-benzyloxycarbonylamino-3-isoxazolidinone and 540 mg of the Compound (73) obtained in Example 73. To the solution was added 325 mg of DCC dissolved in 2 ml of dichloromethane. The mixture was stirred at room temperature for 2 hours. To the reaction solution was added ethyl acetate, and the crystals which separated out were filtered off. The filtrate was washed with water and dried (Na2SO4), 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 553 mg of the subject Compound (75) 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 (Na2SO4)
  5. customby evaporating off the solvent
  6. washfollowed by elution with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-9f492b88bff34eeca0239240a779f7c9
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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