Process for the stereochemical inversion of (2S,3S)-2-amino-3-ph

Details Process for the stereochemical inversion of (2S,3S)-2-amino-3-ph Process for the stereochemical inversion of (2S,3S)-2-amino-3-ph

1990-10-19

1993-04-13

Shah, Mukund J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564304, C07C20900, C07B 5700

Patent

active

052024849

ABSTRACT:
A four step process for transforming (2S,3S)-2-amino-3-phenyl-1,3-propanediols into their (2R,3R)-enantiomers is described. The final compounds are useful intermediates for the synthesis of antibiotics like Chloramphenicol, Thiamphenicol and Florfenicol. The starting products generally are discard products in the synthesis of said antibiotics.

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Jerry March, Advanced Organic Chemistry, 3rd ed. pp. 102-107, 527-529, 796-798, 1057-1060 (1985).
Tetrahedron Letters, vol. 29, No. 43, 1988, pp. 5561-5564, C. Giordano, et al., "New Strategy For Racemization Of 2-Amino-1, 3-Propanediols, Key Intermediates For The Synthesis Of Antibiotic Drugs".
Giordano et al., J. Org. Chem., 1991, vol. 56, No. 21, pp. 6114-6118.
Eliel, "Second-Order Asymmetric Transformation", pp. 62-63 and 38-41.
V. Horak et al., Communications, "Oppenauer Oxidation of 2-Acylamino-1-aryl-1,3-propanediols; A New Method for Racemization of an Optically Active Diastereoisomer", Oct. 1984, pp. 839-840.

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