Hydrochloric Acid → (3S,4R)-1-BOC--4-((S)-1-phenylethylamino)pyrrolidine-3-carboxylic acid

HRID 497503Notes

Reaction equation

HRID 497503 reaction equation
C([O:3][C:4]([C@H:6]1[C@H:10]([NH:11][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH2:9][N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>O1CCCC1>[C:23]([O:22][C:20]([N:8]1[CH2:9][C@@H:10]([NH:11][C@@H:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:13])[C@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[O:21])([CH3:24])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 106900341-(tert-butyl) 3-ethyl (3R,4S)-4-(((R)-1-phenylethyl)amino)pyrrolidine-1,3-dicarboxylate

Product 1

HCID 69748542(3S,4R)-1-BOC--4-((S)-1-phenylethylamino)pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3R,4S)-4-[(R)-1-phenyl-ethylamino]-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (prepared according to the procedure of X. Wang, J. F. Espinosa and S. H. Gellman, J. Am. Chem. Soc. 2000, 122, 4821; 107 mg, 295 μmol) in tetrahydrofuran (2 mL) was treated with 1.0 M sodium hydroxide solution (600 μL, 600 μmol) and the heterogenous mixture was stirred at room temperature. After 18 h, the now homogenous solution was treated with 1.0 M hydrochloric acid (600 μL, 600 μmol) and concentrated in vacuo. The residue was dissolved in water and lyophilized to provide the product, along with sodium chloride, as a white solid (115 mg, quantitative), used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. customto provide the product
  4. customalong with sodium chloride, as a white solid (115 mg, quantitative), used without further purification

Sources & evidence

ORD record
ord-98201dc8beea40f290bd8faf80cb3a74
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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