Ethanol → Ethyl isoleucinate--hydrogen chloride (1/1)

HRID 1821713Notes

Reaction equation

[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].S(Cl)([Cl:12])=O.[CH3:14][CH2:15]O>>[ClH:12].[CH2:14]([O:8][C:7](=[O:9])[C@H:2]([C@H:3]([CH2:5][CH3:6])[CH3:4])[NH2:1])[CH3:15]

Participants

Reactant 3

HCID 702Ethanol

HCID 6306L-Isoleucine

HCID 24386Thionyl Chloride

Product 1

HCID 6453390Ethyl isoleucinate--hydrogen chloride (1/1)

Procedure

L-isoleucine ethyl ester hydrochloride salt was prepared by the procedure in Example 1(B) utilizing L-isoleucine (5.0 g, 38.1 mmol), thionyl chloride (8.3 mL, 11.44 mmol) and EtOH (33.54 mL, 57.15 mmol). The ethyl ester 14t was obtained as a colorless oil (2.5 g, 14.91 mmol, 39%).

Sources & evidence

ORD record: ord-912772c555084e3bbdf7db179746057a
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608599B2

Reaction notes

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