Valeryl chloride → Benzyl(S)-2-((2'-cyanobiphenyl-4-ylmethyl)pentanoylamino)-3-methylbutyrate

HRID 1739082Notes

Reaction equation

HRID 1739082 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[C@H:10]([CH:27]([CH3:29])[CH3:28])[NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31](Cl)(=[O:36])[CH2:32][CH2:33][CH2:34][CH3:35]>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:30])[C@H:10]([CH:27]([CH3:28])[CH3:29])[N:11]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])=[CH:17][CH:18]=1)[C:31](=[O:36])[CH2:32][CH2:33][CH2:34][CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 61186Valeryl chlorideHCID 11112111(2S)-2-(2'-Cyano-4-biphenylylmethylamino)-3-methylbutyric acid benzyl ester

Product 1

HCID 46912012Benzyl(S)-2-((2'-cyanobiphenyl-4-ylmethyl)pentanoylamino)-3-methylbutyrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.2 g (15.5 mmol) of N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine benzyl ester and 8.0 ml of Huinig base, dissolved in 50 ml of methylene chloride, are treated with 2.3 ml of valeryl chloride with stirring and further processed analogously to Example 29b. The title compound is thus obtained as a yellow oil which is further used in crude form (Rf 0.51, toluene-methanol 19:1)

Sources & evidence

ORD record
ord-91fcbddf29324834aae12f10a47c548c
Source dataset
uspto-grants-1999_10
Patent number
US05965592

Reaction notes

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