Triethylamine → HCID 10398325, compound

HRID 1365594Notes

Reaction equation

HRID 1365594 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:13]([N:15](CC)CC)[CH3:14].BrCC#N>CCOC(C)=O>[C:13]([CH2:14][O:11][C:10](=[O:12])[CH2:9][NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])#[N:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11534BromoacetonitrileHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 10398325HCID 10398325, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution containing 2.0 g (11.4 mmol) of Nα-Boc-glycine in 25 mL of EtOAc was added 1.73 g (2.38 mL, 17.1 mmol) of triethylamine followed by 2.05 g (1.19 mL, 17.1 mmol) of bromoacetonitrile. The reaction mixture was stirred at 60° C. under an argon atmosphere for 16 h. The heterogeneous mixture was cooled to room temperature and filtered through a short pad of silica, washing with EtOAc to remove the precipitated triethylamine hydrobromide. The filtrate was concentrated under diminished pressure to give Nα-Boc-glycine cyanomethyl ester as a colorless syrup which solidified upon standing. The crude product was used directly in the next step without further purification: yield 2.12 g (87%); 1HNMR (500 MHz, CDCl3) δ 1.45 (s, 9H), 4.05 (d, 2H, J=5.5 Hz) and 4.79 (s, 2H).

Workup

  1. temperatureThe heterogeneous mixture was cooled to room temperature
  2. filtrationfiltered through a short pad of silica
  3. washwashing with EtOAc
  4. customto remove the precipitated triethylamine hydrobromide
  5. concentrationThe filtrate was concentrated under diminished pressure

Sources & evidence

ORD record
ord-6f1bd472233f45df9689664f3bed0c7c
Source dataset
uspto-grants-2011_02
Patent number
US07893042B2

Reaction notes

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