methyl 2-(benzyloxycarbonylamino)-2-hydroxyacetate synthesis
- Product Name:methyl 2-(benzyloxycarbonylamino)-2-hydroxyacetate
- CAS Number:127357-38-4
- Molecular formula:C11H13NO5
- Molecular Weight:239
Yield:127357-38-4 149.6 g
Reaction Conditions:
with hydrogenchloride in methanol at 56; for 0.666667 h;
Steps:
2.2.i Step 2: Step i:
Step 2: Step i: 2-(((benzyloxy)carbonyl)amino)-2-hydroxyacetic acid 2 (133.0 g, 0.59 mol, 1.0 eq.) was diluted in methanol (480 mL). Trimethyl orthoformate (TMOF, 130.2 mL, 1.11 mol, 2.0 eq.) and hydrochloric acid in methanol (1.25 M, 24 mL, 0.03 mol, 0.05 eq.) were added successively. The mixture was stirred at 56 °C for 40 min. Solvent was concentrated down under reduce pressure and 600 mL of Et20 were added. If necessary starting material was filtered off. The filtrate was concentrated down and dried under reduce pressure. The expected intermediate (149.6 g) was obtained as a white solid. Purity was assessed by NMR, and was >95%. :H NMR (400 MHz, DMSO-dg) δ (ppm) : 3.26 (s, 3H), 3.66 (s, 3H), 5.08 (s, 2H), 5.16 (d, J = 9,2 Hz, 1H), 7.28-7.44 (m, 5H), 8.49 (d, J= 8.8 Hz, 1H).
References:
WO2016/46409,2016,A1 Location in patent:Paragraph 00175
621-84-1
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