Sodium Carbonate → (1S, 2S, 3R)-2,3-bis(hydroxymethyl)-1-cyclobutylamine

反応式

[OH:1][CH2:2][C@@H:3]1[C@@H:6]([CH2:7][OH:8])[CH2:5][C@H:4]1[NH2:9].CC(N(C1C=CC=CC=1)CC(O)=O)=O.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>>[OH:1][CH2:2][C@H:3]1[C@H:6]([CH2:7][OH:8])[CH2:5][C@@H:4]1[NH2:9]

参加物

反応物 4

HCID 10340Sodium Carbonate

HCID 14798Sodium Hydroxide

HCID 516892Sodium Bicarbonate

HCID 131717654(1R, 2R, 3S)-2,3-bis(hydroxymethyl)-1-cyclobutylamine N-acetyl-L-phenylglycine

生成物 1

HCID 55291246(1S, 2S, 3R)-2,3-bis(hydroxymethyl)-1-cyclobutylamine

実験手順

To the (1R, 2R, 3S)-2,3-bis(hydroxymethyl)-1-cyclobutylamine/N-acetyl-L-phenylglycine salt thus isolated is added an alkaline aqueous solution of, for example, sodium hydrogencarbonate, sodium carbonate or sodium hydroxide. Then the mixture is extracted with an organic solvent such as t-butanol or secbutanol. Or a solution of the salt is treated with an ion exchange resin. Then the salt is separated into the aimed free base (1R, 2R, 3S)-2,3-bis(hydromethyl)-1-cyclobutylamine and N-acetyl-L-phenylglycine. On the other hand, (1S, 2S, 3R)-2,3-bis(hydroxymethyl)-1-cyclobutylamine may be produced by the same method as the one described above except that the N-acetyl-L-phenylglycine is replaced by N-acetyl-D-phenylglycine.