Ethanol → HCID 70285014, compound

Participants

Reaction Conditions

Reaction Steps

100 g N-acetyl-indoline-2-carboxylic acid (purity 96.5%) was dissolved in 835 ml of a mixture containing 90% ethanol (EtOH), 5% water and 5% methanol (MeOH), with heating to 60° C., and with mechanical stirring. 54.4 g/0.69 eq. (1S,2S)-1-phenyl-2-amino-1,3-propanediol ([α]20D =+25.7° (c=1, MeOH)) was dosed in portions in 30 min. at 60° C. At the end spontaneous crystallization of the salt took place. After 30 minutes' subsequent stirring at 60-66° C., cooling to 15° C. took place, followed by another 30 minutes' stirring. After filtration over a P4 glass filter, three washings with 120 ml EtOH took place. After air-drying, 68.9 g off-white (S)-N-acetyl-indoline-2-carboxylic acid-(1S,2S)-1-phenyl-2-amino-1,3-propanediol salt was obtained, corresponding to a yield of 37.8%. Enantiomeric excess=96.3% (chiral HPLC).

Provenance & Evidence