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The amide group and the methyl ester on the carbonyl group are both hydrolized by boiling HCI
Posts: 25 Treat phenylalanine with household bleach (strecker degredation) to make phenylacetaldehyde.
Then add H2S04 --sulfuric acid--and a dichromate salt to make chromic acid to oxidise the
I have not tried this but it seems possible, here is what I know of strecker degredation - amino
acids to ketones
Degradation of alpha-Methyl-3,4-dihydroxyphenylalanine
effected oxidatively with sodium hypochlorite1 in 90% yield. Thus, the total sequence (Chart 1)
acetylation, methylation, hydrolysis, and hypochlorite oxidation, can be effected with a potential
The direct hypochlorite oxidation of alpha-methyl-DOPA itself proceeds in the desired manner to
give 3,4-dihydroxyphenylacetone in ca. 50% yield. The latter substance is highly water soluble
a large and competitive extent, however, the direct hypochlorite oxidation of alpha-methyl
DOPA involves nuclear attack as evidenced by accompanying resinification. The use of t-butyl
hypochlorite was found to be superior to sodium hypochlorite in this instance and suggests,
thereby, that the breakdown reaction to ketone is faster than nuclear involvement. The
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Experimental
3,4-Dimethoxyphenylacetone (V) from IV.
Semicarbazone. The semicarbazone crystallized from ether-chloroform and had m.p. 171-174;
mixture melting point was undepressed with an authentic sample of mp 175-176C.
3,4-Dihydroxyphenylacetone (VI)
A. Sodium Hypochlorite
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ml. of water for 50 min. The mixture was cooled, water was added, and it was extracted with
chloroform. The chloroform extract was washed with dilute potassium bicarbonate solution and
salt solution, dried over magnesium sulfate, and concentrated to dryness to give 3,4
diacetoxyphenylacetone (XIV), 9.4 g. (75%); bp 145-150C (0.05 mmHg).
The diacetoxy ketone was converted in good yield by the appropriate processes to the
corresponding dimethoxyketone V and to the dihydroxy hydantoin and alpha-methyl-DOPA.
Similar lead tetraacetate treatment of the N-acetyldimethoxyamino acid IIIc in CH3CN-pyridine
led to the dimethoxy ketone V.
References
1. For the employment of hypochlorite in the degradation of natural amino acids, see:
1. K . Langheld, Ber., 42, 392 (1909)
2 . H . P. Dakin Biochem . J ., 10,319 (1916); 11,79 (1917)
3. D. D. van Slyke, D . A Mcfayden, and D. Hamilton, J. BioI. Chem., 141, 627 (1941)
4.1. D. Spenser, J. C. Crowhall, and D. G. Smyth, Chem. Ind. (London), 798 (1956)
2. Commercial "5%" sodium hypochlorite was used. A 5.00 ml aliquot was added to 2.0 g of
potassium iodide in 30ml of 0.5 N hydrochloric acid and the iodine formed titrated vs . 0.1 N
sodium thiosulfate; 30.50 ml. of 0.1 N sodium thiosulfate was required.
3. Borax buffer: 3.1 g. of boric acid in 50 ml. of water, 8.5 ml. of 1 N sodium hydroxide, and
enough water to bring the total to 100 ml.
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