52558-24-4 (S)-3-(tert-Butyloxycarbonylamino)-2-hydroxypropionic acid

(S) -isoserine 15a (21 g, 0.20 mol) ni tituka ni tetrahydrofuran (100 milimita) Ati iyọdapọ idapọ ti 10percent olomi soda hydroxide ojutu (100 mL), Di-tert-butyl dicarbonate (50 milimita, 0.22 mol) jẹ ti a fi kun dropwise.Iṣe esi naa ni a ṣe ni iwọn otutu yara fun awọn wakati 9. A ṣe atunṣe ipele olomi si pH 2 pẹlu 4 mol / L hydrochloric acid, ti a si fa jade pẹlu dichloromethane / methanol (v / v = 5/1, 50 mL × 3). ) ati ki o si dahùn o lori anhydrous sodium sulfate.Filter nipa afamora, koju labẹ dinku titẹ, Awọn akọle yellow 15b ti a gba bi a colorless epo (35 g, ikore: 85percent).
Si ojutu igbiyanju ti S-isoserine (4.0 g, 0.038 mol) ni dioxane: H2O (100 mL, 1: 1 v / v) ni 0 ° C ti a fi kun N-methylmorpholine (4.77 mL, 0.043 mol), ti o tẹle BoC2O (11.28 milimita, 0.049 mol) ati iṣesi naa ti ru ni alẹ pẹlu imorusi mimu si iwọn otutu yara.Glycine (1.0 g, 0.013 mol) ni a fi kun ati pe a ti ru esi fun iṣẹju 20.Idahun naa ti tutu si O0C o si joko aq.NaHCO3 (75 milimita) ni a ṣafikun.A ti fọ Layer olomi pẹlu ethyl acetate (2 x 60 mL) ati lẹhinna acidified si pH 1 pẹlu NaHSO4.Ojutu yii lẹhinna fa jade pẹlu ethyl acetate (3 x 70 milimita) ati pe awọn fẹlẹfẹlẹ Organic idapo wọnyi ti gbẹ lori Na2SO4, ti a ṣe iyọ ati idojukọ si gbigbẹ lati fun N-Boc-3-ammo-2 (S) ti o fẹ -hydroxy- propanoic acid (6.30 g, 0.031 mmol, 81.5 ogorun ikore): 1H NMR (400 MHz, CDC13) δ 7.45 (bs, 1 H), 5.28 (bs, 1 H), 4.26 (m, 1 H), 3.40-3.62 (m , 2 H), 2.09 (s, 1 H), 1.42 (awọn, 9 H);13C NMR (IOO MHz, CDC13) δ 174.72, 158.17, 82, 71.85, 44.28, 28.45.
N-Boc-3-amino-2 (S) -hydroxy-propionic acid;Si ojutu igbiyanju ti S-isoserine (4.0 g, 0.038 mol) ni dioxane: H2O (100 mL, 1: 1 v / v) ni 0 ° C ti a fi kun N-methylmorpholine (4.77 mL, 0.043 mol), ti o tẹle BoC2O (11.28 milimita, 0.049 mol) ati iṣesi naa ti ru ni alẹ pẹlu imorusi mimu si iwọn otutu yara.Glycine (1.0 g, 0.013 mol) ni a fi kun ati pe a ti ru esi fun iṣẹju 20.Idahun naa ti tutu si 0°C o si joko aq.NaHCO3 (75 milimita) ni a ṣafikun.A ti fọ Layer olomi pẹlu ethyl acetate (2 x 60 mL) ati lẹhinna acidified si pH 1 pẹlu NaHSO4.Ojutu yii lẹhinna fa jade pẹlu ethyl acetate (3 x 70 milimita) ati pe a ti gbẹ awọn fẹlẹfẹlẹ Organic ti o ni idapo lori Na2SO4, ti a yọ ati ki o fojusi si gbigbẹ lati fun N-Boc-3-amino-2 (5) ti o fẹ -hydroxy-propanoic acid (6.30 g, 0.031 mmol, 81.5 ogorun ikore): 1H NMR (400 MHz, CDC13) δ 7.45 (bs, 1 H), 5.28 (bs, 1 H), 4.26 (m, 1 H), 3.40-3.62 (m , 2 H), 2.09 (s, 1 H), 1.42 (awọn, 9 H);13C NMR (100 MHz, CDC13) δ 174.72, 158.17, 82, 71.85, 44.28, 28.45.