Ethyl Acetate → HCID 67001079, compound

HRID 560125Notes

Reaction equation

HRID 560125 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:22])[CH2:9][NH:10][CH2:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[O:13])[CH:5]=[CH:6][CH:7]=1.[O:23](C(OC(C)(C)C)=O)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=O.C([O-])(O)=O.[Na+].C(OCC)(=O)C>C1COCC1.CN(C1C=CN=CC=1)C>[C:27]([O:26][C:24](=[O:23])[N:10]([CH2:9][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[OH:22])[CH2:11][C:12](=[O:13])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 67001032HCID 67001032, compound

Product 1

HCID 67001079HCID 67001079, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To 2-[2-(3-bromo-phenyl)-2-hydroxy-ethylamino]-N-o-tolyl-acetamide (4 g) in THF (100 mL) was added DMAP (134 mg) and (BOC)2O (2.89 g) in THF (100 mL) at 0° C. The mixture was stirred at room temperature for 2 h. An aqueous solution of NaHCO3 and ethyl acetate was added, the phases were separated and the inorganic one was extracted with ethyl acetate (×2). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2, n-heptane/ethyl acetate 1:1,) yielded [2-(3-bromo-phenyl)-2-hydroxy-ethyl]-(o-tolylcarbamoyl-methyl)-carbamic acid tert-butyl ester (0.88 g, 88%) as a colorless oil, MS: 463.1 (M+H, 1Br)+.

Workup

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with ethyl acetate (×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-39059235fe924d5f9f47a171ea458738
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

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