Sulfuric Acid → 3-ethyl-N2-[(S)-1-phenylethyl]-L-norvalinamide

HRID 431283Notes

Reaction equation

HRID 431283 reaction equation
S(=O)(=O)(O)O.[CH2:6]([CH:8]([CH2:21][CH3:22])[C@H:9]([NH:12][C@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])[C:10]#[N:11])[CH3:7].[NH4+].[OH-:24]>>[CH2:21]([CH:8]([CH2:6][CH3:7])[C@@H:9]([C:10]([NH2:11])=[O:24])[NH:12][C@H:13]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:14])[CH3:22]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 11644310(S)-3-ethyl-2-{[(S)-1-phenylethyl]amino}pentanenitrile

Product 1

HCID 669301253-ethyl-N2-[(S)-1-phenylethyl]-L-norvalinamideYield 90%

Conditions

Temperature
25 °C

Procedure

To 25 mL of sulfuric acid at 0° C. was added (S)-3-ethyl-2-{[(S)-1-phenylethyl]amino}pentanenitrile (2.7 g, 11.6 mmol) portionwise. The mixture was warmed to 25° C. After 2 days, the reaction mixture was poured over about 100 g of crushed ice. Concentrated NH4OH was added to neutralize the acid. This mixture was extracted with EtOAc (3×100 mL), dried over Na2SO4, filtered and concentrated to give 3-ethyl-N2-[(S)-1-phenylethyl]-L-norvalinamide (2.6 g, 90%), which was used in the next step without purification. Mass Spectrum (+ESI): 249 (M+H)+. Anal. Calc'd for C15H24N2O: C, 72.54; H, 9.74; N, 11.28. Found: C, 72.24; H, 10.04; N, 11.01

Workup

  1. extractionThis mixture was extracted with EtOAc (3×100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b64699e2b7a84f9c908869117a8adfd5
Source dataset
uspto-grants-2003_12
Patent number
US06657070B2

Reaction notes

Loading…