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

(S)-isoserine 15a (21 g, 0.20 mol) ua hoʻoheheʻe ʻia i ka tetrahydrofuran (100 mL) A ʻo kahi mea hoʻoheheʻe hui ʻia o 10percent aqueous sodium hydroxide solution (100 mL), Di-tert-butyl dicarbonate (50 mL, 0.22 mol) Hoʻohui ʻia ka hāʻule. ) a hoʻomaloʻo ʻia ma luna o ka sodium sulfate anhydrous. E kānana ma ka hoʻomoʻa ʻana, e hoʻomau i lalo o ke kaomi hoʻemi ʻia, Ua loaʻa ka hui inoa 15b ma ke ʻano he aila kala ʻole (35 g, hua: 85percent).
I ka hoʻonā hoʻoulu ʻana o S-isoserine (4.0 g, 0.038 mol) i dioxane: H2O (100 mL, 1:1 v/v) ma 0° C ua hoʻohui ʻia ʻo N-methylmorpholine (4.77 mL, 0.043 mol), a ukali ʻia e BoC2O (11.28 mL, 0.049 mol) a ua hoʻoulu ʻia ka pane ʻana i ka pō me ka hoʻomehana ʻana i ka lumi wela.Hoʻohui ʻia ʻo Glycine (1.0 g, 0.013 mol) a hoʻoulu ʻia ka hopena no 20 min.Ua hooluolu ka pane i ka O0C a noho aq.Hoʻohui ʻia ʻo NaHCO3 (75 mL).Ua holoi ʻia ka ʻili wai me ka ethyl acetate (2 x 60 mL) a laila hoʻāwaʻi ʻia i ka pH 1 me NaHSO4.Lawe ʻia kēia hāpana me ka ethyl acetate (3 x 70 mL) a ua hoʻomaloʻo ʻia kēia mau papa organik i hui ʻia ma luna o Na2SO4, kānana a hoʻopaʻa ʻia i ka maloʻo e hāʻawi i ka N-Boc-3-ammo-2(S)-hydroxy-propanoic acid i makemake ʻia. (6.30 g, 0.031 mmol, 81.5 pakeneka o ka hua): 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 (s, 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 ;I ka hoʻonā hoʻoulu ʻana o S-isoserine (4.0 g, 0.038 mol) i ka dioxane: H2O (100 mL, 1:1 v/v) ma 0° C ua hoʻohui ʻia ʻo N-methylmorpholine (4.77 mL, 0.043 mol), a ukali ʻia e BoC2O (11.28 mL, 0.049 mol) a ua hoʻoulu ʻia ka pane ʻana i ka pō me ka hoʻomehana ʻana i ka lumi wela.Hoʻohui ʻia ʻo Glycine (1.0 g, 0.013 mol) a hoʻoulu ʻia ka hopena no 20 min.Hoʻomaha ʻia ka hopena i 0 ° C a noho aq.Hoʻohui ʻia ʻo NaHCO3 (75 mL).Ua holoi ʻia ka ʻili wai me ka ethyl acetate (2 x 60 mL) a laila hoʻāwaʻi ʻia i ka pH 1 me NaHSO4.Lawe ʻia kēia hāpana me ka ethyl acetate (3 x 70 mL) a ua hoʻomaloʻo ʻia kēia mau papa organik i hui ʻia ma luna o Na2SO4, kānana a hoʻopaʻa ʻia i ka maloʻo e hāʻawi i ka N-Boc-3-amino-2(5)-hydroxy-propanoic acid i makemake ʻia. (6.30 g, 0.031 mmol, 81.5 pakeneka o ka hua): 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 (s, 9 H);13C NMR (100 MHz, CDC13) δ 174.72, 158.17, 82, 71.85, 44.28, 28.45.