Ammonium Chloride → HCID 67372163, compound

HRID 1677058Notes

Reaction equation

HRID 1677058 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[CH3:10][CH2:11][O:12][C:13]([C@H:15]1[CH2:19][CH2:18][C:17](=[O:20])[N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:14].[Cl-].[NH4+]>O1CCCC1>[CH2:11]([O:12][C:13](=[O:14])[C@H:15]([NH:16][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:18][C:17]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:20])[CH3:10]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 8208851-Boc-D-Pyroglutamic acid ethyl esterHCID 178418676HCID 178418676, compound

Product 1

HCID 67372163HCID 67372163, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 4-fluorophenyl magnesium bromide (25.6 mL, 1 M tetrahydrofuran solution) was added dropwise at −40° C. into a tetrahydrofuran (100 mL) solution containing (R)-5-oxopyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-ethyl ester (6 g). After stirring for 1 hour at the same temperature, saturated ammonium chloride aqueous solution was added, and the resultant was extracted with ethyl acetate. After washing the organic layer with brine, the resultant was dried over anhydrous magnesium sulfate. After removing the solvent under a vacuum, the residue was purified with silica gel column chromatography, and the title compound (6.33 g) was obtained. The physical property values are as follows.

Workup

  1. additionwas added
  2. extractionthe resultant was extracted with ethyl acetate
  3. washAfter washing the organic layer with brine
  4. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  5. customAfter removing the solvent under a vacuum
  6. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-463ec8f8895b42b5996d5081f6b74caf
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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