HCID 131724098, compound → HCID 87222126, compound

Participants

Reaction Steps

Nα-tert-butyloxycarbonyl-L-serine (4.59 g, 22.3 mmol) was dissolved in N,N-dimethylformamide (100 mL), the solution was then cooled to 0° C. and treated with sodium hydride (1.97 g, 49.2 mmol). 1-Bromo-2-(2-methoxyethoxy)ethane (10.0 g, 49.2 mmol) was added to the solution and the reaction mixture was stirred at ambient temperature for 3 h. The solvent was then removed under a reduced pressure at 40° C. bath temperature. The residue was dissolved in water (75 mL) and washed twice with diethyl ether (30 mL each time). The aqueous layer was then acidified to pH 3 with 1M HCl and then extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4 and the solvent was removed in vacuo to yield the compound as a yellow oil (4.1 g, 63%). The compound has the following characteristics: FTIR (CHCl3): 1735 (vCO, s), 1712 (vCO, s). 1H NMR (CDCl3): δ5.63 (d, (CH3)3COC(O)NHCH(CH2OCH2CH2OCH2CH2O CH3)C(O)OH, 1H), 4.14-3.53 (m, (CH3)3COC(O)NHCH(CH2OCH2CH2O—CH2CH2OCH3)C(O)OH, 1H), 4.14-3.53 (m, (CH3)3COC(O)NHCH(CH2OCH2CH2O—CH2CH2OCH3)C(O)OH, 10 H), 3.47 (s, (CH3)3COC(O)NHCH(CH2OCH2CH2OCH2—CH2OCH3)C(O)OH, 3H), 1.52 (s, (CH3)3COC(O)NHCH(CH2O—CH2CH2OCH2CH2—OCH3)C(O)OH, 9H). MALDITOF-MS: MH+: 307.34 calcd, 309.19 found.

Provenance & Evidence