تفاعل #510086
ord-c27c689e56d3463badf453e23109f4b3
معادلة التفاعل
المتفاعلات
الكواشف
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المعالجة
- 1أخرىThe ice/water cooling bath was removed
- 2تركيزAfter concentration under reduced pressure
- 3أخرىthe residue was partitioned between water and CH2Cl2
- 4غسيلthe combined organic layers were washed with brine
- 5تجفيفdried over sodium sulfate
- 6ترشيحfiltered
- 7تركيزconcentrated under reduced pressure
- 8أخرىThe crude product was purified by silica gel flash column chromatography
- 9غسيلeluting with 0 to 50% ether in hexane
الإجراء التجريبي
To a 25 ml pear-shaped flask containing 2-(S-t-butylsulfanylmethyl)-3-(3-bromophenyl)propionic acid (0.22 g, 0.665 mmol) and THF (7 ml), at 0° C. were added dropwise a solution of glycine benzyl ester hydrochloride (0.134 g, 0.665 mmol) and a solution of triethylamine (93 μl, 67.3 mg, 0.665 mmol) in CH2Cl2 (7 ml), followed by dropwise additions of a solution of HOBT (0.102 g, 0.665 mmol) in THF (5 ml) and a solution of 1,3-dicyclohexyl carbodiimide (0.164 g, 0.796 mmol) in CH2Cl2 (6 ml). The ice/water cooling bath was removed and the mixture was stirred at room temperature overnight. After concentration under reduced pressure, the residue was partitioned between water and CH2Cl2, and the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel flash column chromatography eluting with 0 to 50% ether in hexane to give 2-[3-(3-bromophenyl)-2-(S-t-butylsulfanylmethyl)propionylamino]acetic acid benzyl ester as a colorless viscous oil, 0.25 g, 79% yield. HPLC purity: 100%. 1H NMR (CDCl3) δ 1.29 (s, 9H), 2.51 (m, 1H), 2.64 (m, 1H), 2.85 (m, 3H), 4.02 (m, 2H), 5.16 (s, 2H), 5.95 (m, 1H), 7.12 (m, 2H), 7.35 (m, 7H); MS (ES+) [M+H+]: 478, 480; (ES−) [M−H+]: 476, 478.