BOC-SER-OH synthesis
- Product Name:BOC-SER-OH
- CAS Number:59524-02-6
- Molecular formula:C15H21NO5
- Molecular Weight:295.33
3262-72-4
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100-39-0
425 suppliers
$10.00/10 g
59524-02-6
177 suppliers
$5.00/1g
Yield:59524-02-6 100%
Reaction Conditions:
Stage #1:(S)-N-(tert-butoxycarbonyl)serine with caesium carbonate in N,N-dimethyl-formamide for 0.5 h;
Stage #2:benzyl bromide in N,N-dimethyl-formamide for 12 h;Product distribution / selectivity;
Steps:
1
To a stirring solution of N-Boc- (L) -Serine (4.87 mmol) in DMF (100 mL) was added cesium carbonate (5.11 mmol) and stirring was continued 30 minutes. Benzyl bromide (5.84 mmol) was then added and the resulting solution was stirred 12 hours. The reaction mixture was then diluted with ethyl acetate (25 mL), washed with lithium bromide (3 x 15 mL), sodium bicarbonate (2 x 15 mL), and brine (2 x 15mL). The organic layer was dried over sodium sulfate. The solvent was then removed under reduced pressure and the resulting tan oil was purified by flash chromatography, using 1: 1 petroleum ether/diethyl ether, to afford the product (100%) as a white solid. Rf= 0. 26 (1: 1 petroleum ether/diethyl ether).; To a stirring solution of N-Boc- (L) -Serine (2.44 mmol) in DMF (50 mL) was added cesium carbonate (2. 56 mmol) and stirring was continued 30 minutes. Benzyl bromide (2. 92 mmol) was then added and the resulting solution was stirred 12 hours. The reaction mixture was then diluted with ethyl acetate (15 mL), washed with lithium bromide (3 x 10 mL), sodium bicarbonate (2 x 10 mL), and brine (2 x 10 mL). The organic layer was dried over sodium sulfate. The solvent was then removed under reduced pressure and the resulting tan oil was purified by flash chromatography, using 1: 1 petroleum ether/diethyl ether, to afford the product (100%) as a white solid. Rf= 0.26 (1: 1 petroleum ether/diethyl ether).
References:
UNIVERSITY OF VIRGINIA PATENT FOUNDATION WO2005/41899, 2005, A2 Location in patent:Page/Page column 94; 102-103
56-45-1
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24424-99-5
823 suppliers
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100-39-0
425 suppliers
$10.00/10 g
59524-02-6
177 suppliers
$5.00/1g
24424-99-5
823 suppliers
$13.50/25G
3695-68-9
13 suppliers
$57.29/5 g
59524-02-6
177 suppliers
$5.00/1g
24424-99-5
823 suppliers
$13.50/25G
59524-02-6
177 suppliers
$5.00/1g
24424-99-5
823 suppliers
$13.50/25G
1738-72-3
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$79.00/5g
59524-02-6
177 suppliers
$5.00/1g