Hydrochloric Acid → tert-butyl 3(3-pentyl)-L-phenylalaninate

HRID 429920Notes

Reaction equation

HRID 429920 reaction equation
[CH3:1][CH2:2][CH:3]([C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][CH:17]=1)[CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])[CH2:4][CH3:5].Cl.[CH3:19][C:20](=[CH2:22])[CH3:21]>O1CCOCC1>[CH3:5][CH2:4][CH:3]([C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][CH:17]=1)[CH2:9][C@@H:10]([C:12]([O:14][C:20]([CH3:22])([CH3:21])[CH3:19])=[O:13])[NH2:11])[CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8255IsobutyleneHCID 206376833-(3-pentyl)-L-phenylalanine

Product 1

HCID 20637699tert-butyl 3(3-pentyl)-L-phenylalaninateYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

According to example 54, 0.60 g of 3-(3-pentyl)-L-phenylalanine.HCl was treated with 30 mL of isobutylene in 35 mL of 1,4-dioxane in the presence of 0.5 mL of conc. H2S4. Work-up in the usual manner followed by acidification with 2 mL of 1N ethereal HCl afforded 0.53 g (74%) of tert-butyl 3(3-pentyl)-L-phenylalaninate.HCl as a light yellow glass.

Sources & evidence

ORD record
ord-6b404b233d5c4043bb4e4c6b826cc7d9
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

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