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L-Pyroglutamic Acid → tert-Butyl 5-oxo-L-prolinate

HRID 10418
Notes
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Reaction equation

HRID 10418 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].Cl(O)(=O)(=O)=O.[OH-].[Na+].C(O[C:21]([CH3:24])([CH3:23])[CH3:22])(=O)C>O>[O:6]=[C:5]1[NH:1][C@H:2]([C:7]([O:9][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:8])[CH2:3][CH2:4]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7405L-Pyroglutamic AcidHCID 10908tert-Butyl acetateHCID 14798Sodium HydroxideHCID 24247Perchloric Acid

Product 1

HCID 10888648tert-Butyl 5-oxo-L-prolinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

129 g of L-pyroglutamic acid were suspended in 2 l of tert-butyl acetate. 30 ml of a 70% strength solution of perchloric acid in water were added thereto. The mixture was then stirred at room temperature for 12 h. It was cooled to 0° C. and the pH of the solution was adjusted to 7 by cautious addition of a 2N NaOH solution. The phases were separated and the organic phase was washed twice with 300 ml of a saturated sodium chloride solution each time. The organic phase was then dried with sodium sulfate. The solvents were removed in vacuo, and the residue was stirred with heptane. The solid obtained in this way was filtered off with suction. The mother liquor was concentrated in vacuo, and the solid obtained in this way was also filtered off with suction.

Workup

  1. temperatureIt was cooled to 0° C.
  2. customThe phases were separated
  3. washthe organic phase was washed twice with 300 ml of a saturated sodium chloride solution each time
  4. dry with materialThe organic phase was then dried with sodium sulfate
  5. customThe solvents were removed in vacuo
  6. stirringthe residue was stirred with heptane
  7. customThe solid obtained in this way
  8. filtrationwas filtered off with suction
  9. concentrationThe mother liquor was concentrated in vacuo
  10. customthe solid obtained in this way
  11. filtrationwas also filtered off with suction

Sources & evidence

ORD record
ord-d12afd9173344f0ea591ca507c1e1ff0
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07094800B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes