Hydrochloric Acid → 5-[(Carboxymethyl-methoxycarbonyl-amino)-methyl]-pyrrolidine-2-carboxylic acid ethyl ester

HRID 71737Notes

Reaction equation

HRID 71737 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH:8]([CH2:11][N:12]([CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[C:13]([O:15][CH3:16])=[O:14])[N:7]1C(OC(C)(C)C)=O)=[O:5].Cl>O1CCOCC1>[CH2:2]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH:8]([CH2:11][N:12]([CH2:17][C:18]([OH:20])=[O:19])[C:13]([O:15][CH3:16])=[O:14])[NH:7]1)=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666203185-[(Tert-butoxycarbonylmethyl-methoxycarbonyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Product 1

HCID 666202125-[(Carboxymethyl-methoxycarbonyl-amino)-methyl]-pyrrolidine-2-carboxylic acid ethyl esterYield 114.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-[(tert-Butoxycarbonylmethyl-methoxycarbonyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (304 mg, 0.68 mmol) was added to a solution of hydrogen chloride in dioxane (4N, 15 mL). After 16 hours the solvent was removed under reduced pressure and the resulting residue was azeotroped with toluene to provide 5-[(carboxymethyl-methoxycarbonyl-amino)-methyl]-pyrrolidine-2-carboxylic acid ethyl ester (224 mg)—assumed 100% yield.

Workup

  1. customAfter 16 hours the solvent was removed under reduced pressure
  2. customthe resulting residue was azeotroped with toluene

Sources & evidence

ORD record
ord-e5fbcf0a3c7a4a05a8668ed8d74bfd12
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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