Ethyl Acetate → HCID 69754678, compound

HRID 967718Notes

Reaction equation

HRID 967718 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH3:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.[CH2:13]([O:20][C:21](=[O:27])[NH:22][CH:23]([CH3:26])[CH2:24]Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[CH2:13]([O:20][C:21](=[O:27])[NH:22][CH:23]([CH3:24])[CH2:26][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=2)[C:2]([Cl:1])=[N:3]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 69752289HCID 69752289, compoundHCID 178487535HCID 178487535, compound

Product 1

HCID 69754678HCID 69754678, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Step C (0.18 g, 1 mmol) and (2-bromo-1 methyl-ethyl)-carbamic acid benzyl ester (0.27 g, 1 mmol) in DMF (2 mL) was added potassium carbonate (0.17 g, 1.2 mmol) and the mixture stirred at 75° for 18 h. Ethyl acetate (20 mL) and water (20 mL) were added to the reaction mixture and the aqueous layer was separated and extracted with ethyl acetate (3×20 mL). The combined extracts were washed with brine (30 mL), dried (MgSO4), and evaporated to a residue that was purified by chromatography (silica, hexane to 15% ethyl acetate in hexane) to give a syrup (0.27 g): APCl/LCMS m/z 374 (M+H)+.

Workup

  1. customthe aqueous layer was separated
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined extracts were washed with brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a residue that
  6. customwas purified by chromatography (silica, hexane to 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-619fe4104c704c13a01ec9b67072fb0c
Source dataset
uspto-grants-2005_10
Patent number
US06956036B1

Reaction notes

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