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

HRID 1609197Notes

Reaction equation

HRID 1609197 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.CCN(C(C)C)C(C)C.[C:40](Cl)(=[O:45])[CH2:41][CH2:42][CH2:43][CH3:44]>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:40](=[O:45])[CH2:41][CH2:42][CH2:43][CH3:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 61186Valeryl chlorideHCID 81531DiisopropylethylamineHCID 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 Hunig 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-1ab919209ed046bf946fd12c3ce6b49f
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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