(R,S)-N-benzoyl-2-((2R)-1-bromopropoxy)-5-fluorophenylglycine synthesis
- Product Name:(R,S)-N-benzoyl-2-((2R)-1-bromopropoxy)-5-fluorophenylglycine
- CAS Number:1134785-08-2
- Molecular formula:C18H17BrFNO4
- Molecular Weight:410.23
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Yield:1134785-08-2 293 g (83%)
Reaction Conditions:
in methanesulfonic acid;
Steps:
A.18 2-Benzoylamino-2-[2-(R-2-bromo-1-methylethoxy)-5-fluorophenyl]acetic Acid
PREPARATION A18 2-Benzoylamino-2-[2-(R-2-bromo-1-methylethoxy)-5-fluorophenyl]acetic Acid The product of the preceding Preparation (193 g, 0.86 mol) was added in a slow stream to cold methanesulfonic acid (620 ml) with the aid of mechanical stirring. The resulting solution was then maintained at less than 15° C., while N-benzoyl-alpha-hydroxyglycine (156 g, 0.8 mol, alpha-hydroxyhippuric acid) was added thereto in several portions over a period of 20 minutes. The resulting reaction mixture was then allowed to warm slowly to room temperature and stirred for 40 hours. The viscous solution thus obtained was then poured over 1.5 liters ice with constant agitation to precipitate the crude product as a yellow solid. The latter material was subsequently collected by means of suction filtration, washed with water and then ethanol, and air-dried to constant weight to afford 293 g (83%) of title product; m.p. 203°-210° C. 1 H-NMR(DMSO-d6)delta(ppm): 8.9 (t, 1H), 8.2-7.1 (m, 8H), 6.1 (d, 2H), 4.7 (m, 1H), 3.7 (d, 2H), 1.3 (dd, 3H).
References:
US4853410,1989,A
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