N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → HCID 104700691, compound

A mixture of IClSO3H (5 g, 42.91 mmol) and ClCH2Br (5.55 g, 42.9 mmol) was refluxed for 3 hours, followed by pouring into ice. The ice water suspension was extracted with DCM (2×50 mL), and the combined DCM layers were washed with water (2×50 mL) to give a solution of ClCH2SO3Cl (solution A). A solution of Boc-β-Ala-OH (12, 4.73 g, 25 mmol), NaHCO3 (8.41 g, 100 mmol), and Bu4N+HSO4− (0.849 g, 2.5 mmol) in water (100 mL) was cooled to 0° C., followed by addition of solution A. The mixture was stirred vigorously for 2 hours, followed by separation of the layers. The DCM layer was washed with brine (2×100 mL), and dried over anhydrous MgSO4. The solvent was removed in vacuo and the residue purified by silica gel column chromatography (20% EtOAc in hexane, v/v) to yield 1.2 g (20%) of product (13): 13C NMR δ 28.218 (3×CH3 of Boc), 34.439 (CH2C(═O)O), 35.655 (NHCH2CH2), 68.565 (OCH2Cl), 79.547 (C(CH3)3), 155.811 (NHC(═O)O), 170.761 (C(═O)O).

1. customfollowed by separation of the layers
2. washThe DCM layer was washed with brine (2×100 mL)
3. dry with materialdried over anhydrous MgSO4
4. customThe solvent was removed in vacuo
5. customthe residue purified by silica gel column chromatography (20% EtOAc in hexane, v/v)

ORD record

ord-698bdd0f11a141c7befe3825c1b72bc7

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07033583B2