Potassium tert-butoxide → tert-butyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate

HRID 1518302노트

반응식

HRID 1518302 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][CH:25]=[C:26]([C:28](OC)=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].[CH3:40][C:41]([O-:44])([CH3:43])[CH3:42].[K+]>C(OC(C)(C)C)(=O)C.C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][CH:25]=[C:26]([C:28]([O:44][C:41]([CH3:43])([CH3:42])[CH3:40])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]

참가 물질

5

반응물 2

HCID 23665647Potassium tert-butoxide2회HCID 59447536HCID 59447536, 화합물

생성물 1

HCID 59447538tert-butyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 10908tert-Butyl acetate용매

실험 절차

To a stirring solution of methyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate (38A) (14 g, 24.1 mmol) in t-butyl acetate (200 mL) was added 2 mL of t-BuOK in THF (2M) under vacuum. 3×2 mL t-BuOK were added to the stirring solution under vacuum to drive the reaction to complete. The mixture was then acidified to neutrality and washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with 5% EtOAc in hexanes to provide 3.5 g of the desired product 38B: 1H NMR (300 MHz, CDCl3) δ ppm 8.29 (1H, m), 7.71 (1H, d), 7.62 (2H, m), 7.49 (2H, t), 7.34 (3H, m), 6.02 (2H, s), 5.20 (2H, s), 4.02 (2H, m), 3.71 (3H, m), 3.08 (2H, m), 1.59 (9H, t), 0.97 (2H, m), −0.09 (9H, m). MS (ESI(+)): m/z 623.0 (M+H).

후처리

  1. customthe reaction
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by column chromatography on silica gel eluting with 5% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-0f05c560488340f6bf5cb0437c559675
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232273B2

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