Dimethylformamide → HCID 20610270, compound

HRID 433662Notes

Reaction equation

HRID 433662 reaction equation
CN(C)C=O.[C:6]([O:10][C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[C:18]1[CH:22]=[C:21]([CH2:23]Br)[O:20][N:19]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[CH2:25]([O:27][C:28](=[O:42])[CH:29]([NH:35][C:36]([O:38][CH2:39][CH:40]=[CH2:41])=[O:37])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:26].C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)C>[CH2:33]([O:32][C:30](=[O:31])[C:29]([NH:35][C:36]([O:38][CH2:39][CH:40]=[CH2:41])=[O:37])([CH2:23][C:21]1[O:20][N:19]=[C:18]([CH:14]2[CH2:15][CH2:16][CH2:17][N:13]2[C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[CH:22]=1)[C:28]([O:27][CH2:25][CH3:26])=[O:42])[CH3:34]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 20610271HCID 20610271, compoundHCID 20610321HCID 20610321, compound

Product 1

HCID 20610270HCID 20610270, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A dimethyl formamide (260 mL) solution of 2-(5-Bromomethyl-isoxazol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (7.29 g, 56 mmol) and 2-allyloxycarbonylamino-malonic acid diethyl ester (8.25 g, 32 mmol) was cooled to 0° C. and cesium carbonate (25.41 g, 78 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 3 hours. The reaction mixture was then poured into diethyl ether (2 L) and washed with water (5×200 mL) and brine. The organic portion was dried over magnesium sulfate and concentrated in vacuo. The crude residue was chromatographed on silica gel eluting with ethyl acetate:hexane (3:7) to afford the title compound as a clear colorless oil (10.95 g; 83%). MS (Cl) m/z 260.1 (M-99).

Workup

  1. washwashed with water (5×200 mL) and brine
  2. dry with materialThe organic portion was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was chromatographed on silica gel eluting with ethyl acetate:hexane (3:7)

Sources & evidence

ORD record
ord-8c18de4330464b78ac884cb782ed8bb1
Source dataset
uspto-grants-2003_12
Patent number
US06667331B2

Reaction notes

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