ChemicalBook CAS DataBase List N-Carbobenzyloxy-L-alanine

N-Carbobenzyloxy-L-alanine synthesis

7synthesis methods

Product Name:N-Carbobenzyloxy-L-alanine
CAS Number:1142-20-7
Molecular formula:C11H13NO4
Molecular Weight:223.23

28819-05-8
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$6.00/250mg

1142-20-7
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$5.00/1g

Yield:1142-20-7 98%

Reaction Conditions:

Stage #1:(S)-2-benzyloxycarbonylamino-propionic acid methyl ester with sodium hydroxide in ethanol;water at 20; for 0.666667 h;
Stage #2: with hydrogenchloride in ethanol;water; pH=2

Steps:

2
5 g (21 mmol) of compound 3 was dissolved in 50 ml of ethanol, 30 ml of 2.5 mM NaOH was added. The reaction was stirred at room temperature for 40 minutes, acidified with 6N HCl to about pH 2. The combined extracts were washed twice with saturated NaCl solution, dried (Na₂SO₄). The solvent was removed to give 4.59 g (98%) of the desired product as white solid or clear oil. ¹H NMR (500 MHz, CDCl₃): δ 7.34-7.27 (m, 5H), 5.39 (br, 1H), 5.11 (s, 2H), 4.38 (q, J=7.2 Hz, 1H), 1.43 (d, J=7.2 Hz, 3H). ¹³C NMR (125 MHz, CDCl₃): δ 177.78, 155.98, 136.16, 128.68, 128.39, 128.28, 67.27, 49.59, 18.49.

References:

Development Center for Biotechnology US2006/287500, 2006, A1 Location in patent:Page/Page column 2; 3

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56-41-7 Synthesis