1,2-Dichloroethane → 2-Amino-pentanedioic acid 5-tert-butyl ester 1-ethyl ester

HRID 347598Notes

Reaction equation

HRID 347598 reaction equation
[NH2:1][C@H:2]([C:12]([OH:14])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH2:15](Cl)[CH2:16]Cl.C1C=CC2N(O)N=NC=2C=1>C(O)C>[CH2:15]([O:13][C:12](=[O:14])[CH:2]([NH2:1])[CH2:3][CH2:4][C:5]([O:6][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:11])[CH3:16]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 7010573(2S)-2-amino-5-(tert-butoxy)-5-oxopentanoic acid

Product 1

HCID 587038522-Amino-pentanedioic acid 5-tert-butyl ester 1-ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A dry 250 mL round-bottomed flask was charged with 2.200 g (10.800 mmol) H-Glu(O-t-Bu)-OH (41a) dissolved in 100 mL ethanol. To this was added 4.4 g (22.9 mmol) EDC and 3.2 g (23.7 mmol) HOBt. The reaction mixture was stirred at ambient temperature for 22 h. The reaction mixture was followed to completion according to the LC-MS data. The solvent was removed under reduced pressure and the resulting oil was dissolved in dichloromethane 300 mL and extracted with H2O 300 mL. The H2O-phase was adjusted to pH 9.5. The crude product was extracted into dichloromethane 400 mL, dried over NaSO4, filtrated and evaporated.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting oil was dissolved in dichloromethane 300 mL
  3. extractionextracted with H2O 300 mL
  4. extractionThe crude product was extracted into dichloromethane 400 mL
  5. dry with materialdried over NaSO4
  6. filtrationfiltrated
  7. customevaporated

Sources & evidence

ORD record
ord-182a3e3987f9471fb45124ab42384b52
Source dataset
uspto-grants-2007_02
Patent number
US07175767B2

Reaction notes

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