反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][NH2:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)([C:18]1[CH:26]=[CH:25][C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=1)(=O)=O.[OH:28][S:29](O)(=O)=[O:30]>C1COCC1.[OH-].[Na+].O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][NH:14][S:29]([C:20]1[CH:19]=[CH:18][CH:26]=[CH:25][C:21]=1[N+:22]([O-:24])=[O:23])(=[O:30])=[O:28])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]参加物
反応条件
- 温度
- -10 °C
実験手順
(S)-2-tert-Butoxycarbonylamino-3-amino-propionic acid (14.9 g, 73.2 mmol) was dissolved in a mixture of THF (45 mL) and 3 N aq. NaOH (45 mL). The reaction mixture was cooled to −10° C. and nosyl chloride (17.9 g, 80.5 mmol) was added as a THF solution (75 mL) drop wise over 30 min. The reaction mixture was stirred at −10° C. for 45 min followed by stirring at ambient temperature for 30 min. The reaction mixture was diluted with water (150 mL), acidified with 2% aqueous H2SO4 (to pH ˜2) and diluted with additional water (450 mL). The product was extracted with EtOAc (600 mL total) and washed with water (3×400 mL) and brine (100 mL). The organic layer was separated, dried over Na2SO4, filtered and condensed in vacuo to afford compound A (20.0 g, 70% yield) as a cream solid. LC-MS [M+H-Boc] 290.3 (C14H19N3O8S+H, calc: 390.4). Purity >95% (UV/254 nm). Compound A was used without further purification.
後処理
- stirringby stirring at ambient temperature for 30 min
- extractionThe product was extracted with EtOAc (600 mL total)
- washwashed with water (3×400 mL) and brine (100 mL)
- customThe organic layer was separated
- dry with materialdried over Na2SO4
- filtrationfiltered
- customcondensed in vacuo
出典と根拠
- ORDレコード
- ord-bbb50ff3d8a9465e848dbe9b3a05d037
- 出典データセット
- uspto-grants-2015_05
- 特許番号
- US09040032B2
関連ノート
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