Hydrochloric Acid → HCID 57775865, compound

HRID 1753692Notes

Reaction equation

HRID 1753692 reaction equation
[C:1]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br-].[Mg+2].[Br-].Cl>C1COCC1>[C:4]([O:3][C:1]([NH:8][C@@H:9]([CH2:10][CH2:11][C:12](=[O:13])[CH:5]=[C:4]([CH3:7])[CH3:6])[C:14]([OH:16])=[O:15])=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 82241Magnesium BromideHCID 1044121,2-Pyrrolidinedicarboxylic acid, 5-oxo-, 1-(1,1-dimethylethyl) ester, (2S)-

Product 1

HCID 57775865HCID 57775865, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of N-Boc-pyroglutamic acid (0.23 g 1.0 mmol) in 10.0 ml of anhydrous THF was added 2-methylprop-1-enyl)magnesium bromide (0.5 M in THF, 5 mL, 2.5 mmol) at −78° C. slowly. The reaction mixture was stirred for 1 h at −78° C. 1 N HCl (2.5 ml) aqueous solution was added and the mixture was slowly warmed up to RT. The pH was adjusted to ˜3 by 1 N HCl. The THF was then removed under vacuum and the remaining aqueous was extracted by DCM (3×20 mL). The organic layer was dried over Na2SO4, filterd and the solvent was removed to provide the crude product.

Workup

  1. temperaturethe mixture was slowly warmed up to RT
  2. customThe THF was then removed under vacuum
  3. extractionthe remaining aqueous was extracted by DCM (3×20 mL)
  4. dry with materialThe organic layer was dried over Na2SO4, filterd
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-5b8aeb11720d4a468a2ce07cddd34751
Source dataset
uspto-grants-2015_10
Patent number
US09163061B2

Reaction notes

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