Potassium tert-butoxide → HCID 86680443, compound

HRID 240432Notes

Reaction equation

HRID 240432 reaction equation
C([O:9][C@H:10]1[C@@H:14]2[CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18][N:13]2[CH2:12][CH2:11]1)(=O)C1C=CC=CC=1.CC(C)([O-])C.[K+]>CO>[OH:9][C@H:10]1[C@@H:14]2[CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18][N:13]2[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 89466305HCID 89466305, compound

Product 1

HCID 86680443HCID 86680443, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 35E (8 g, 0.023 mol) in methanol (25 mL) was added potassium t-butoxide (14.5 g, 0.129 mol), and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated, the residue was diluted with 5% citric acid in water (100 mL), and the mixture was extracted with ethyl acetate (50 mL×2). The combined organic layers were discarded. The aqueous layer was basified using K2CO3 to pH 8-9 and extracted with ethyl acetate (50 mL×2). The combined organic layers were dried over Na2SO4 and concentrated to give the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.48 (s, 9H), 1.56-1.69 (m, 1H), 1.86-1.97 (m, 1H), 2.10-2.35 (m, 3H), 2.35-2.48 (m, 1H), 2.52-2.72 (m, 1H), 2.78-2.97 (m, 2H), 3.03 (dt, 1H, J=17.1, 2.4 Hz), 3.92-4.15 (m, 2H), 4.32 (bs, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with 5% citric acid in water (100 mL)
  3. extractionthe mixture was extracted with ethyl acetate (50 mL×2)
  4. extractionextracted with ethyl acetate (50 mL×2)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1e82b89d1ea04a2098b40f1f25985131
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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