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

HRID 1609191Notes

Reaction equation

HRID 1609191 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:31])[C@H:11]([CH:28]([CH3:30])[CH3:29])[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]#[N:27])=[CH:16][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[C:41](Cl)(=[O:46])[CH2:42][CH2:43][CH2:44][CH3:45]>>[CH2:2]([O:9][C:10](=[O:31])[C@H:11]([CH:28]([CH3:29])[CH3:30])[N:12]([C:41](=[O:46])[CH2:42][CH2:43][CH2:44][CH3:45])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]#[N:27])=[CH:18][CH:19]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 61186Valeryl chlorideHCID 81531DiisopropylethylamineHCID 44252740HCID 44252740, compound

Product 1

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

Procedure

5.5 g of N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine benzyl ester hydrochloride, 4.33 g of diisopropylethylamine and 3 ml of valeryl chloride are stirred at room temperature for 36 hours and the mixture is then evaporated to dryness. The residue is taken up in ether and washed with sodium bicarbonate and brine. The crude product is further processed without purification.

Workup

  1. customthe mixture is then evaporated to dryness
  2. washwashed with sodium bicarbonate and brine
  3. customThe crude product is further processed without purification

Sources & evidence

ORD record
ord-8a66b5ec68df4ef1969c5f907b78076b
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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