methyl(R)-3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate synthesis

7synthesis methods

Product Name:methyl(R)-3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate
CAS Number:318249-44-4
Molecular formula:C13H17NO5
Molecular Weight:267.28

Benzenesulfonamide, 4-methyl-N-[(3R)-tetrahydro-5-oxo-3-furanyl]-

162518-06-1
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methyl(R)-3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate

318249-44-4
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Yield:-

Reaction Conditions:

with trimethylamine in methanol;chloroform;

Steps:

4 Preparation of the Methylester of (R)-4-hydroxy-3-(benzyloxycarbonylamino) Butanoic Acid 5a (Step d)

EXAMPLE 4 Preparation of the Methylester of (R)-4-hydroxy-3-(benzyloxycarbonylamino) Butanoic Acid 5a (Step d) Compound 4 (2.35 g, 10 mmol) (Y=benzyloxycarbonyl, prepared as described in J. Am. Chem. Soc. 1986, 108, 4943-4952) was solubilized in MeOH (15 mL) and added with 18.8 mL (80 mmol) of 25% trimethylamine in MeOH by weight. The reaction was left to stir at room temperature for three days, whereupon CHCl₃ was added and the organic phase was washed with HCl 1N and then with NaCl s.s. The organic phase was dried on Na₂SO₄, filtered and vacuum evaporated to dryness to yield 2.27 g of an oil containing 90% of product (as shown by NMR analysis) and 10% of starting product; ¹H NMR (CDCl₃): δ 7.35 (s, 5H), 5.45 (br, 1H), 5.10 (s, 2H), 4.08 (m, 1H), 3.75 (d, 2H), 3.65 (s, 3H), 2.65 (d, 2H), 1.60 (brs, 1H). This product was used as such in the following reaction.

References:

US2003/153783,2003,A1

67-56-1 Synthesis