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 1518302Notes

Reaction equation

HRID 1518302 reaction equation
[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]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxide2×HCID 59447536HCID 59447536, compound

Product 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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 10908tert-Butyl acetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0f05c560488340f6bf5cb0437c559675
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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