Synthesis of chiral α-substituted β-hydroxy acid derivatives on solid support

Tetrahedron Letters

Volumn 38, Issue 51, 1997, Pages 8777-8780

  Purandare, Ashok V ^a   Natarajan, Sesha ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ESTER; HYDROXYACID;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; TECHNIQUE;

EID: 0030733231     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10378-1     Document Type: Article

References (8)

1. Evans, D. A; Bartoli, J.; Shih, T. L.; J. Am. Chem. Soc. 1981, 103, 2127.
2. Kurth, M. J.; Randall, L. A.; Chen, C.; Melander, C.; Miller, R. B.; McAllister, K.; Reitz, G; Kang, R.; Nakatsu, T.; Green, C.; J. Org. Chem. 1994, 59, 5862.
3. Allin, S. M.; Shuttleworth, S. J; Tetrahedron Letters 1996, 37, 8023.
4. Richter, L. H.; Gadek, T. R.; Tetrahedron Letters. 1994, 35, 4705.
5. Ho, G. J; Mahtre, D. J; J. Org. Chem. 1995, 60, 2271.
6. 2 (each 3 × 5 mL) and finally with methanol.
7. Procedure For Cleavage (to ester): A solution of sodium methoxide (1.0 mL, 25% solution in methanol) was added to a cooled (-20°) suspension of resin (6) (125 mg) in THF (4 mL) placed in a fritted funnel fitted with a stopcock. The reaction mixture was vortexed for 1 h and the reaction was quenched by addition of acetic acid (20 mL). The solution was filtered and the filtrate was concentrated in vacuo to a crude mixture containing 7 and 8. The crude was purified by column chromatography (silica gel, hexane-ethyl acetate; 8:2) to furnish analytically pure 7 (26 mg) and 8 (3mg).
8. 2, -20° to 0°; 3) NaOMe, THF, -20°.