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

HRID 1169252Notes

Reaction equation

HRID 1169252 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. 1H NMR (300 mHz, CD3OD) δ7.48 (m, 5H), 4.44 (m, 1H), 3.89 (m, 1H), 3.78 (m, 1H), 3.44-3.14 (3H), 1.67 (d, 3H), 1.4 (bs, 9H); mass spec. (ES+) m/z 335.3.

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-8cb7e8a9d55d4edaac313100e97f1b79
Source dataset
uspto-grants-2003_09
Patent number
US06627629B2

Reaction notes

Loading…