Benzyl Bromide → HCID 11044573, compound

HRID 1612880Notes

Reaction equation

[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([C:3]([C:1]#[N:2])([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 2

HCID 7498Benzyl Bromide

HCID 7764Ethyl cyanoacetate

Product 1

HCID 11044573HCID 11044573, compoundYield 80%

Procedure

Ethyl cyanoacetate (15.0 g, 0.133 mol) was dialkylated with benzyl bromide employing 1,8-diazabicyclo[5.4.0]undecene-7 as described by: Ono, N.; Yoshimura, T.; Tanikaga, R.; Kaji, A. Chem. Lett. 1977, 871-872. The obtained ethyl 2-benzyl-2-cyano-3-phenylpropionate (80% yield) was identical with the material described in Example 88. The ester was saponified to the corresponding carboxylic acid as previously described in Example 88. The title peptide was prepared under standard solid phase peptide conditions as examplified in Examples 1 and 2.

Sources & evidence

ORD record: ord-55518e9ba424475791aa380530e83fbc
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05190922

Reaction notes

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