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ChemicalBook CAS DataBase List Caprylylglycine

Caprylylglycine synthesis

7synthesis methods
-

Yield:14246-53-8 83%

Reaction Conditions:

with sodium hydroxide in water;acetone

Steps:

V Preparation of N-octanoyl glycine
Preparation of N-octanoyl glycine Glycine (11.25 g; 0.15 mol) was dissolved in water (50 ml), sodium hydroxide (12 g 0.3 mol) added and the mixture stirred. To this solution octanoyl chloride (24.4 g; 0.15 mol) in acetone (50 ml) was added dropwise with vigourous stirring over 1 hour. The mixture was further stirred for 1 hour at room temperature and, thereafter, concentrated to dryness under reduced pressure to give a white solid. This solid was boiled with ether (3 x 150 ml); filtered and then the combined ethereal layers washed with brine (150 ml). It was then dried over sodium sulphate filtered and concentrated under vacuo. The resulting white solid (27 g, 83% yield) mpt 105-106°C was used in the experiment described in Table II. 1Hnmr (δ, CD3OD) 3.9 (S, 2H, HN CH 2CO2H), 2.25 (t, 2H, CH 2 CONH), 1.6 (t, 2H, CH 2-CH2 CO, 1.3 (m, 8H,- (CH2)4 -CH2CH2CO), 0.9(t, 3H, CH 3-(CH2)4).

References:

UNILEVER PLC;UNILEVER N.V. EP540279, 1993, A1

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