Chloroacetic Acid → HCID 54366311, compound

To a solution of O-(2-amino-3-hydroxy-4,4,4-trifluoro-1-oxobutyl)-N-trifluoroacetyl-L-serine (685 mg) and chloroacetic acid (0.04 ml) in water (7 ml) was added sodium nitrite (227 mg) at room temperature. After stirring for 30 minutes at room temperature, the reaction mixture was neutrized with 2M tris buffer solution to pH 7.0 to 7.3 and then Acylase I (acylase, Sigma A-7264, made by Sigma Chemicals) (140 mg) was added. The mixture was stirred for 6 hours at room temperature and chromatographed on carbon (60 ml) eluting successively with water and a 9:1 mixture of water and acetone to give a crude product, which was chromatographed on preparative thin layer chromatography eluting with a 65:35:4 mixture of chloroform, methanol and water, and lyophilized to give O-(2-diazo-3-hydroxy-4,4,4-trifluoro-1-oxobutyl)-L-serine (113 mg).

1. additionAcylase I (acylase, Sigma A-7264, made by Sigma Chemicals) (140 mg) was added
2. stirringThe mixture was stirred for 6 hours at room temperature
3. customchromatographed on carbon (60 ml)
4. washeluting successively with water
5. additiona 9:1 mixture of water and acetone
6. customto give a crude product, which
7. customwas chromatographed on preparative thin layer chromatography
8. washeluting with a 65:35:4 mixture of chloroform, methanol and water

ORD record

ord-1eaa9ab9b8c247c0b06b52167e811c69

Source dataset

uspto-grants-1990_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04939241