Acetic Acid → (2S,5S)-5-(2-benzylamino-2-carboxyethyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

HRID 10422Notes

Reaction equation

HRID 10422 reaction equation
[CH2:1]([NH:8][CH:9]([C:30](=[O:32])N)[CH2:10][C@H:11]1[N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:14]([C:23]([O:25]C(C)(C)C)=[O:24])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=[O:37])C>C(O)C.O>[C:19]([O:18][C:16]([N:15]1[C@H:11]([CH2:10][CH:9]([NH:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:30]([OH:37])=[O:32])[CH2:12][CH2:13][C@H:14]1[C:23]([OH:25])=[O:24])=[O:17])([CH3:21])([CH3:22])[CH3:20]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 86760185di-tert-butyl (2S,5S)-5-(2-benzylamino-2-carbamoylethyl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 69643721(2S,5S)-5-(2-benzylamino-2-carboxyethyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2.2 g of di-tert-butyl (2S,5S)-5-(2-benzylamino-2-carbamoylethyl)pyrrolidine-1,2-dicarboxylate were dissolved in 20 ml of ethanol and 5 ml of water. 1.2 g of solid sodium hydroxide were added thereto. The solution was then boiled under reflux for 36 h. For workup, it was cooled to room temperature and neutralized with acetic acid, and the ethanol was removed in vacuo. The residue was diluted with 20 ml of water and adjusted to a pH of 3 with acetic acid. The mixture was extracted 3 times with 30 ml of 5:1 ethyl acetate/butanol each time. The organic phases were combined and concentrated in vacuo. The residue was chromatographed on silica gel.

Workup

  1. temperatureunder reflux for 36 h
  2. customthe ethanol was removed in vacuo
  3. additionThe residue was diluted with 20 ml of water
  4. extractionThe mixture was extracted 3 times with 30 ml of 5:1 ethyl acetate/butanol each time
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-e2f54db65abf48f99044f31ef5758d3e
Source dataset
uspto-grants-2006_08
Patent number
US07094800B2

Reaction notes

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