Potassium Carbonate → (S)-tert-butyl 4-((1,1-diethoxypropan-2-ylamino)methyl)benzo[d]thiazol-2-ylcarbamate
반응식
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH2:7])[CH3:6])[CH3:2].Br[CH2:12][C:13]1[C:18]2[N:19]=[C:20]([N:22](C(OC(C)(C)C)=O)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[S:21][C:17]=2[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH:7][CH2:12][C:13]1[C:18]2[N:19]=[C:20]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[S:21][C:17]=2[CH:16]=[CH:15][CH:14]=1)[CH3:6])[CH3:2]참가 물질
5
반응 조건
- 온도
- 65 °C
실험 절차
To a solution of (S)-1,1-diethoxypropan-2-amine (Compound XVIII-1) (442 mg, 3.00 mmol) in acetonitrile (5 ml) were added 4-bromomethyl-2-bis(tert-butoxycarbonyl)aminobenzothiazole (Compound XX-1) (133 mg, 0.30 mmol) and potassium carbonate (62 mg, 0.45 mmol) and the mixture was stirred at 65° C. for 2 hr. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate (100 ml) and the mixture was washed with water (100 ml) and brine (100 ml). The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (eluent: chloroform:methanol=100:0 to 95:5) to obtain the title compound (173 mg, yield: 71%).
후처리
- concentrationThe reaction mixture was concentrated in vacuo
- additionthe residue was diluted with ethyl acetate (100 ml)
- washthe mixture was washed with water (100 ml) and brine (100 ml)
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
- customthe residue was purified by silica gel column chromatography (eluent: chloroform:methanol=100:0 to 95:5)
출처 및 근거
- ORD 기록
- ord-f89241b128694ad89eab0846294e35b3
- 출처 데이터셋
- uspto-grants-2015_09
- 특허 번호
- US09126981B2
반응 노트
불러오는 중…