Dicyclohexylcarbodiimide → HCID 67901861, compound

HRID 232230Notes

Reaction equation

HRID 232230 reaction equation
[CH3:1][O:2][CH:3]([C:20]([O-:22])=[O:21])[CH2:4][C:5](=O)[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=[O:7].[CH2:23]([O:30][C:31]([NH:33][C@H:34]1[CH2:38][O:37][NH:36][C:35]1=[O:39])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH2:23]([O:30][C:31]([NH:33][C@H:34]1[CH2:38][O:37][N:36]([C:5]2([C:6]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=3)=[O:7])[CH2:4][CH:3]([O:2][CH3:1])[C:20](=[O:21])[O:22]2)[C:35]1=[O:39])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14181640HCID 14181640, compoundHCID 67902313HCID 67902313, compound

Product 1

HCID 67901861HCID 67901861, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 10 ml of dichloromethane was dissolved 896 mg of Compound (93). To the solution were added 680 mg of (4S)-4-benzyloxycarbonylamino-3-isoxazolidinone and 593 mg of DCC, and the mixture was stirred at room temperature for one hour. Then, precipitating crystals were filtered off, and the solvent was evaporated off. The residue was subjected to a silica gel column chromatography, followed by elution with hexane--ethyl acetate (3:2) to give 723 mg of the subject Compound (94) as an oily product.

Workup

  1. customThen, precipitating crystals
  2. filtrationwere filtered off
  3. customthe solvent was evaporated off
  4. washfollowed by elution with hexane--ethyl acetate (3:2)

Sources & evidence

ORD record
ord-9f9d8d815f4145bbbbf55d6f45a20a66
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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