Potassium tert-butoxide → HCID 68312970, compound

HRID 1530434Notes

Reaction equation

HRID 1530434 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9](=[O:38])[CH:10]([O:14][C:15]1[CH:37]=[CH:36][C:18]2[C:19]3[N:23]([CH2:24][CH2:25][O:26][C:17]=2[CH:16]=1)[CH:22]=[C:21]([C:27]1[N:28]([CH:33]([CH3:35])[CH3:34])[N:29]=[C:30]([CH3:32])[N:31]=1)[N:20]=3)[CH2:11][CH2:12]Br>C1COCC1.O>[CH3:7][O:8][C:9]([C:10]1([O:14][C:15]2[CH:37]=[CH:36][C:18]3[C:19]4[N:23]([CH2:24][CH2:25][O:26][C:17]=3[CH:16]=2)[CH:22]=[C:21]([C:27]2[N:28]([CH:33]([CH3:35])[CH3:34])[N:29]=[C:30]([CH3:32])[N:31]=2)[N:20]=4)[CH2:12][CH2:11]1)=[O:38]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 68313022HCID 68313022, compound

Product 1

HCID 68312970HCID 68312970, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium tertbutoxide (611 mg, 5.45 mmol) was added to a solution of 4-bromo-2-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]butyric acid methyl ester (2.5 g, 4.96 mmol) in THF (20 mL) and the mixture was stirred at RT for 30 min. The crude reaction mixture was diluted with water and extracted with EtOAc (×3). The combined organic layers were washed with brine, then dried and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-7% MeOH in DCM) affording 1-[2-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]cyclopropanecarboxylic acid methyl ester (1.4 g, 67%). 1H NMR (CDCl3, 400 MHz): δ 8.42 (1H, d, J=8.98 Hz), 7.56 (1H, s), 6.75 (1H, dd, J=8.97, 2.58 Hz), 6.58 (1H, d, J=2.55 Hz), 5.97-5.82 (1H, m), 4.50-4.35 (4H, m), 3.74 (3H, s), 2.40 (3H, s), 1.67-1.60 (2H, m), 1.55 (6H, d, J=6.52 Hz), 1.38-1.31 (2H, m)

Workup

  1. customThe crude reaction mixture
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 0-7% MeOH in DCM)

Sources & evidence

ORD record
ord-dcd8d18cf3ce42f5810dbadb1fab0678
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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