반응 #450397
ord-7088a151dbb849f09ea1cedc475809c7
반응 방정식
반응물
시약
반응 조건
후처리
- 1workup.STIRRINGthe reaction mixture was stirred
- 2온도to warm to 25 ° C. over 2.5 h
- 3workup.WAITThe reaction mixture was left
- 4온도to warm to ambient temperature overnight
- 5기타Solvent was removed
- 6workup.ADDITIONthe residue treated with H2O (200 mL)
- 7추출extracted with EtOAc (3×150 mL)
- 8세척The organics were washed with H2O, brine
- 9건조dried (MgSO4 and DARCO)
- 10여과filtered
- 11농축concentrated
- 12기타to give a yellow oil
- 13온도cooled to 0° C.
- 14기타to precipitate the title compound as a tan solid
실험 절차
1-Naphthylmethanol (5.0 g, 0.0316 mol) was dissolved in dry CH2Cl2 (30 mL), diisopropylethylamine (6.6 mL, 0.0379 mol) was added, and the solution was cooled to 0° C. in an ice-water bath under Ar. Methanesulfonyl chloride (3.2 mL, 0.0316 mol) was added dropwise. After stirring cold for 30 min, additional diisopropylethylamine (1.6 mL) and methanesulfonyl chloride (0.8 mL) were added, and the reaction mixture was stirred and allowed to warm to 25 ° C. over 2.5 h. This solution was added alternately dropwise with diisopropylethylamine (22.5 m, 0.129 mol) to a slurry of glycine methyl ester hydrochloride (19.8 g, 0.158 mol) and diisopropylethylamine (5 mL, 0.028 mol) in dry DMF (30 mL) at 0° C. The reaction mixture was left to warm to ambient temperature overnight. Solvent was removed, and the residue treated with H2O (200 mL) and extracted with EtOAc (3×150 mL). The organics were washed with H2O, brine, and dried (MgSO4 and DARCO), filtered and concentrated to give a yellow oil. The oil was dissolved in EtOAc (200 mL), cooled to 0° C., and treated with HCl gas to precipitate the title compound as a tan solid. 1H NMR (CDCl3) δ10.48 (br s, 2H), 8.23 (d, 1H, J=8.6 Hz), 7.85-7.9 (m, 3H), 7.65 (td, 1H, J=1, 10 Hz), 7.47-7.58 (m, 2H), 4.84 (s, 2H), 3.67 (s, 3H), 3.65 (s, 2H).