Dicyclohexylcarbodiimide → Boc-beta-cyano-L-alanine

HRID 58896

Reaction equation

HRID 58896 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([NH:23][C@H:24]([C:29]([OH:31])=[O:30])[CH2:25][C:26](=O)[NH2:27])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CC(C)=O.N1C=CC=CC=1>[C:19]([O:18][C:16]([NH:23][C@@H:24]([CH2:25][C:26]#[N:27])[C:29]([OH:31])=[O:30])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 82035N2-((tert-Butoxy)carbonyl)-L-asparagine

Product 1

HCID 7019873Boc-beta-cyano-L-alanineYield 64.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1049PyridineSolvent

Procedure

A solution of dicyclohexylcarbodiimide (DCC, 8.3 g, 40 mmol) in acetone (100 ml) was added dropwise a suspension of Boc-asparagine (9.3 g, 40 mmol) in pyridine (50 mL) at 0° C. under nitrogen. The reaction mixture was stirred at ambient temperature for 3 h. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in dichloromethane (400 mL) and the solution was washed with 2 N aqueous HCl (20 mL×3) and brine (200 mL), dried over anhydrous sodium sulfate, and concentrated to afford (S)-2-(tert-butoxycarbonylamino)-3-cyanopropanoic acid (5.5 g, 56% yield), which was used directly without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in dichloromethane (400 mL)
  4. washthe solution was washed with 2 N aqueous HCl (20 mL×3) and brine (200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9fbf77c1d7c74834977d81de168ffeb4
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Linked notes

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