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

HRID 1805949

반응식

HRID 1805949 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-af38c9975eda47a49ab16f97631878bd
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354548B2

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