Potassium Carbonate → HCID 86607622, compound

HRID 1272576Notes

Reaction equation

HRID 1272576 reaction equation
C([O:5][C:6](=[O:11])[CH2:7][CH2:8][CH2:9]Br)(C)(C)C.[C:12]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:24])[CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C=O)C.CCOC(C)=O>[C:6]([CH2:7][CH2:8][CH2:9][CH:13]([C:12]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])([OH:11])=[O:5]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 84754Dibenzyl malonateHCID 2757253tert-Butyl 4-bromobutanoate

Product 1

HCID 86607622HCID 86607622, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl-4-bromobutyrate (10 mmol) in DMF (100 mL) was treated with dibenzyl malonate (20 mmol) and potassium carbonate (30 mmol) at 40° C. overnight. EtOAc (200 mL) and saturated aqueous ammonium chloride (100 mL) were added and the separated organic layer was washed with 1N HCl (50 mL), saturated aqueous ammonium chloride (100 mL), brine (100 mL), and water (100 mL). After removal of the solvent in vacuo, the crude product was dissolved in dichloromethane (60 mL) and treated at room temperature with trifluoroacetic acid (15 mL) for 2 h. Removal of the solvent in vacuo afforded the crude product, which was purified by reverse phase preparative HPLC using 0.05% TFA/CH3CN/H2O as the mobile phase. The title compound (37) (2 g) was obtained as a colorless oil. 1H NMR (CD3OD, 400 MHz): δ 7.3 (m, 10H), 5.1 (q, 4H), 3.5 (t, 1H), 2.3 (t, 2H), 1.9 (q, 2H), 1.6 (m, 2H). MS (ESI) m/z 370.4 (M+H)+.

Workup

  1. washthe separated organic layer was washed with 1N HCl (50 mL), saturated aqueous ammonium chloride (100 mL), brine (100 mL), and water (100 mL)
  2. customAfter removal of the solvent in vacuo
  3. dissolutionthe crude product was dissolved in dichloromethane (60 mL)
  4. additiontreated at room temperature with trifluoroacetic acid (15 mL) for 2 h
  5. customRemoval of the solvent in vacuo
  6. customafforded the crude product, which
  7. customwas purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-3aedd5c5d59e4fc0b003e298d777b06f
Source dataset
uspto-grants-2007_04
Patent number
US07208611B2

Reaction notes

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