Ammonium Chloride → (S)-2-tert-Butoxycarbonylamino-5-oxo-non-8-enoic acid benzyl ester

HRID 1261854Notes

Reaction equation

HRID 1261854 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C@H:9]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([Mg]Br)[CH2:25][CH:26]=[CH2:27].[Cl-].[NH4+]>C1COCC1>[CH2:17]([O:16][C:14](=[O:15])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11][C:12](=[O:13])[CH2:27][CH2:26][CH:25]=[CH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 80274822-Benzyl 1-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylateHCID 178418797HCID 178418797, compound

Product 1

HCID 67092604(S)-2-tert-Butoxycarbonylamino-5-oxo-non-8-enoic acid benzyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (Org. Lett. 2004, 5, 1469; 450 mg, 1.41 mmol) in THF (10 mL) was added 3-butenylmagnesium bromide solution (0.5 M in THF, 3.38 mL, 1.69 mmoL) at −40° C., then after 3 h sat. aq. ammonium chloride solution (5 mL) was added. The reaction mixture was partitioned between EtOAc and water, the organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc 2:1) afforded the title compound (329 mg, 62%). Colourless oil, MS: 376.4 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6ba98ebed0c34c8cba68ffa3c531d306
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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