Hydrochloric Acid → HCID 57775865, compound

HRID 1877321Notes

Reaction equation

HRID 1877321 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, filtered 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
  5. filtrationfiltered
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-ba61c9bbad294be3b56b390dd1e61aa1
Source dataset
uspto-grants-2012_11
Patent number
US08309685B2

Reaction notes

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