2-Cyanopropanoic acid → HCID 86760524, compound

HRID 853730Notes

Reaction equation

HRID 853730 reaction equation
Cl.[C:2]([O:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])([CH3:5])([CH3:4])[CH3:3].[C:12]([CH:14]([CH3:18])[C:15](O)=O)#[N:13].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(N(CC)CC)C>[C:2]([O:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH:9][CH2:15][CH:14]([C:12]#[N:13])[CH3:18])([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 3528552-Cyanopropanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11275390tert-Butyl alaninate hydrochloride

Product 1

HCID 86760524HCID 86760524, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of alanine tert-butyl ester hydrochloride (41.5 g, 228 mmol) in anhydrous dimethyl formamide (DMF, 35 mL) under argon was added triethylamine (35 mL) followed by 2-cyanopropionic acid (25 g, 252 mmol) and 1-hydroxybenzotriazole hydrate (HOBt, 40.5 g, 300 mmol). The resulting mixture was cooled to 0° C. and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC, 48.8 g, 255 mmol) was added. The mixture was stirred at 0° C. for 2 h followed by 12 h at 23° C. The solvent was removed in vacuo, and the resulting residue was suspended in 300 mL of ethyl acetate. The organic layer was extracted with saturated aqueous NaHSO4 and the precipitate that formed from the emulsion was filtered out. The organic layer was again extracted with saturated aqueous NaHCO3 and saturated aqueous NaCl, dried over anhydrous MgSO4 and concentrated to a viscous yellow oil. 1H NMR (CDCl3): δ 1.4 (dd, 3H, CH3—CH—NH—), 1.5 (s, 9H, (CH3)3), 1.6 (dd, 3H, CH3—CH—CN—), 3.5 (q, 1H, NH—CH—CO2Bu), 4.4 (m, 1H, CH3—CH—CN), 6.8 (s, 1H, NH).

Workup

  1. waitfollowed by 12 h at 23° C
  2. customThe solvent was removed in vacuo
  3. extractionThe organic layer was extracted with saturated aqueous NaHSO4
  4. customthe precipitate that formed from the emulsion
  5. filtrationwas filtered out
  6. extractionThe organic layer was again extracted with saturated aqueous NaHCO3 and saturated aqueous NaCl
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated to a viscous yellow oil

Sources & evidence

ORD record
ord-8a4a932f03384acfa10c96c530f12b6c
Source dataset
uspto-grants-2007_08
Patent number
US07255874B1

Reaction notes

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