Ammonium Chloride → ethyl (R)-2-tert-butoxycarbonylamino-5-(4-chlorophenyl)-5-oxopentanoate

HRID 1677071Notes

Reaction equation

HRID 1677071 reaction equation
[Cl: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]([Cl:1])=[CH:3][CH:4]=1)=[O:20])[CH3:10]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 8208851-Boc-D-Pyroglutamic acid ethyl esterHCID 178478191HCID 178478191, compound

Product 1

HCID 67371186ethyl (R)-2-tert-butoxycarbonylamino-5-(4-chlorophenyl)-5-oxopentanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 4-chlorophenyl magnesium bromide (64.1 mL, 1 M tetrahydrofuran solution) was added dropwise at −40° C. into a tetrahydrofuran (300 mL) solution of (R)-5-oxopyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-ethyl ester (15 g) obtained in Example 4. After stirring for 1 hour at the same temperature, saturated ammonium chloride aqueous solution was added, and extraction with ethyl acetate was conducted. After washing the organic layer with brine, the resultant was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the residue was purified by silica gel column chromatography (heptane→heptane/ethyl acetate), and the title compound (17.38 g) was obtained. The physical property values are as follows.

Workup

  1. additionwas added
  2. extractionextraction with ethyl acetate
  3. washAfter washing the organic layer with brine
  4. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  5. customThe solvent was removed under a vacuum
  6. customthe residue was purified by silica gel column chromatography (heptane→heptane/ethyl acetate)

Sources & evidence

ORD record
ord-04fc8ce35e8f4309875475c83ded476f
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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