Glycine tert-butyl ester → Tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate

HRID 1805949

反応式

HRID 1805949 の反応式
[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[CH:8]=2)[O:3]1.[NH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:14])=[O:13])[CH:8]=2)[O:3]1

参加物

6

反応物 2

HCID 151417Glycine tert-butyl esterHCID 27797742,2-Dimethyl-6-Chromanesulfonyl Chloride

生成物 1

HCID 58409094Tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate収率 88%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

To the solution of 2,2-dimethylchroman-6-sulfonyl chloride (3.165 g, 10.92 mmol) in DCM (50 mL) at −30° C. was added tert-butyl 2-aminoacetate (2.308 mL, 16.39 mmol), Hunig'sBase (3.82 mL, 21.85 mmol), and catalytic amount of DMAP. The mixture was stirred at 25° C. overnight while the reddish orange color of the reaction mixture turned bright yellow. The crude reaction mixture was diluted with EtOAc, washed with dilute aqueous hydrochloric acid solution, then aqueous NaHCO3 solution and brine. The organic layer was dried over MgSO4 and removed on a rotavapor to give a creamy powder. The crude material was purified by silica chromatography (15-30% EtOAc/Hexanes) to yield 3.6 grams of an off white powder (88%). 1H NMR (500 MHz, CDCl3) δ 7.58 (d, J=2.1 Hz, 1H), 7.55 (dd, J=8.6, 2.3 Hz, 1H), 6.81 (t, J=10.6 Hz, 1H), 4.90 (s, 1H), 3.64 (d, J=5.1 Hz, 2H), 2.81 (t, J=6.7 Hz, 2H), 1.81 (t, J=6.7 Hz, 2H), 1.35 (s, 9H), 1.34 (s, 6H). LRMS [ESI, (M−H)−] m/z calcd for C17H24NO5S 354.14, found 354.2.

後処理

  1. customThe crude reaction mixture
  2. washwashed with dilute aqueous hydrochloric acid solution
  3. dry with materialThe organic layer was dried over MgSO4
  4. customremoved on a rotavapor
  5. customto give a creamy powder
  6. customThe crude material was purified by silica chromatography (15-30% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-af38c9975eda47a49ab16f97631878bd
出典データセット
uspto-grants-2013_01
特許番号
US08354548B2

関連ノート

読み込み中…