Ethyl 2-cyano-2-propylvalerate → HCID 11218176, compound

HRID 2185145Notes

Reaction equation

HRID 2185145 reaction equation
C([O:3]C(=O)CN(CCC)CCC)C.[CH2:14]([C:17]([C:26]#[N:27])([CH2:23][CH2:24][CH3:25])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:15][CH3:16]>>[CH2:21]([O:20][C:18](=[O:19])[C:17]([CH2:23][CH2:24][CH3:25])([CH2:14][CH2:15][CH3:16])[C:26]([NH2:27])=[O:3])[CH3:22]

Participants

3

Reactant 2

HCID 99502Ethyl 2-cyano-2-propylvalerateHCID 575237N,N-Dipropylglycine ethyl ester

Product 1

HCID 11218176HCID 11218176, compoundYield 81%

Procedure

The synthesis of this compound, which can also be called di-n-propylglycine ethyl ester, was later optimized (P. M. Hardy, l. N. Lingham, Int. J. Peptide Protein Res. 21, 392-405 (1983)). The synthesis of ethyl 2,2-di-n-propylcyanoacetate 2 gave a yield of 81%, while the subsequent reaction to give the 2,2-di-n-propylmalonic acid monoamide ethyl ester 3 gave a yield of 82%. Following further reaction with bromine and NaOH in CHCl3 at low temperature, the N-bromoamide 4 was not isolated, but, following treatment with a 4-fold excess of sodium hydroxide solution, the corresponding isocyanate 6 in a distillative yield of 81% was obtained. The latter was then refluxed with an excess of 3M HCl. Subsequent alkalinization with sodium hydroxide solution gave the amino ester 5 in a yield of 87%. The overall yield of this synthesis was about 47% starting from cyanoacetic ester 1.

Workup

  1. customThe synthesis of this compound, which
  2. customgave a yield of 81%
  3. customwhile the subsequent reaction

Sources & evidence

ORD record
ord-fbecb5a9278a41e1bd8ca29f493ed91c
Source dataset
uspto-grants-2002_06
Patent number
US06399809B1

Reaction notes

Loading…