HCID 14181640, compound → HCID 14798654, compound

HRID 232196Notes

Reaction equation

HRID 232196 reaction equation
O=[C:2]([CH2:16][CH2:17][C:18]([O-:20])=[O:19])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)=[O:4].[CH2:21]([O:28][C:29]([NH:31][C@H:32]1[CH2:36][O:35][NH:34][C:33]1=[O:37])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl.B(F)(F)F.CCOCC>[CH2:21]([O:28][C:29]([NH:31][C@H:32]1[CH2:36][O:35][N:34]([C:2]2([C:3]([O:5][CH2:6][C:7]3[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=3)=[O:4])[CH2:16][CH2:17][C:18](=[O:19])[O:20]2)[C:33]1=[O:37])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 14181640HCID 14181640, compoundHCID 221664155-[(4-Nitrophenyl)methoxy]-4,5-dioxopentanoate

Product 1

HCID 14798654HCID 14798654, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 6344DichloromethaneSolvent

Procedure

In 5 ml of dichloromethane were dissolved 155 mg of Compound (1) and 119 mg of (4S)-4-benzyloxycarbonylamino-3-isoxazolidinone. To the solution were added two drops of boron trifluoride etherate (47% ether solution) and 2 g of Molecular Sieves (3A). The mixture was allowed to stand at room temperature for 2 days. The reaction solution, after removing the Molecular Sieves, was washed with a cooled aqueous solution of sodium hydrogen carbonate, followed by drying (MgSO4). The solvent was evaporated off under reduced pressure, and the residue was purified by subjecting to a silica gel preparative thin-layer chromatography [developed with 1,2-dichloroethane-ethyl acetate (5:1)] to give 12.5 mg of the subject Compound (9).

Workup

  1. customThe reaction solution, after removing the Molecular Sieves
  2. washwas washed with a cooled aqueous solution of sodium hydrogen carbonate
  3. dry with materialby drying (MgSO4)
  4. customThe solvent was evaporated off under reduced pressure
  5. customthe residue was purified

Sources & evidence

ORD record
ord-c4b49d8d204444ebbc239fb8bcb5e13d
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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