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

HRID 16343
Notes
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Reaction equation

HRID 16343 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.O1CCCC1.[CH3:15][CH2:16][O:17][C:18]([C@H:20]1[CH2:24][CH2:23][C:22](=[O:25])[N:21]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:19]>O>[CH2:16]([O:17][C:18](=[O:19])[C@H:20]([NH:21][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:23][C:22]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:25])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 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 962WaterSolvent

Procedure

4-Chlorophenyl magnesium bromide (1.0 M diethylether solution, 17.1 mL) was dropwise added to a tetrahydrofuran solution (100 mL) of (R)-5-oxopyrrolidin-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (CAS Register No. 128811-48-3, 4.0 g) over 20 min at −40° C. The resulting reaction solution was stirred while heating from −40° C. to 0° C. for 1 hr. To this solution, water was gradually added at 0° C. The reaction solution was extracted with ethyl acetate. The extract solution was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to give 5.6 g of the title compound as a colorless oily substance. The physical property values of this compound were as follows:

Workup

  1. customThe resulting reaction solution
  2. temperaturewhile heating from −40° C. to 0° C. for 1 hr
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. washThe extract solution was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-bea5e79778174509a562f27c6f69c90b
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737141B2

Reaction notes

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