1,2-Dichloroethane → (3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
반응식
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:11]([OH:13])=O.Cl.[CH3:22]OCN.C(Cl)CCl.C1C=C[C:33]2[N:38]([OH:39])N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1>[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:11]([N:38]([O:39][CH3:22])[CH3:33])=[O:13]참가 물질
7
반응물 5
생성물 1
시약·촉매·용매 1
실험 절차
Boc-D-Tic-OH (14.9 g, 53.7 mmol), methoxymethylamine hydrochloride (5.24 g, 53.7 mmol), EDC (11.3 g, 59.1 mmol), HOBT (7.98 g, 59.1 mmol), DIEA (9.83 ml, 59.1 mmol) and THF (500 ml) were combined, and the resulting mixture was stirred for about 18 hours at r.t. under nitrogen. The reaction mixture was concentrated and the residue was taken up in ethyl acetate. The resulting mixture was washed with 1M HCl, saturated NaHCO3 and brine, which was then dried via filtration through phase separator paper. Removal of solvent gives a residue, which was chromatographed on silica gel using (1:1 ethylacetate /hexane) to give about 12.3 g of Boc-D-Tic-NMeOMe (Weinreb amide).
후처리
- concentrationThe reaction mixture was concentrated
- washThe resulting mixture was washed with 1M HCl, saturated NaHCO3 and brine, which
- customwas then dried via filtration through phase
- customRemoval of solvent
- customgives a residue, which
- customwas chromatographed on silica gel using (1:1 ethylacetate /hexane)
출처 및 근거
- ORD 기록
- ord-748448a956a34aad9fc45f7d6ef29a73
- 출처 데이터셋
- uspto-grants-2007_11
- 특허 번호
- US07291619B2
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