Sodium Bicarbonate → HCID 57937818, compound

HRID 1435062Notes

Reaction equation

HRID 1435062 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][NH:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[CH3:15].C(=O)(O)[O-].[Na+].[C:21]([O:25][C:26](=O)[O:27]C(C)(C)C)([CH3:24])([CH3:23])[CH3:22]>C(OCC)(=O)C>[C:21]([O:25][C:26](=[O:27])[N:7]([CH2:6][C:5]1[CH:13]=[CH:14][C:2]([Br:1])=[C:3]([CH3:15])[CH:4]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 57937846HCID 57937846, compound

Product 1

HCID 57937818HCID 57937818, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

(4-bromo-3-methyl-benzyl)-(3-methyl-butyl)-amine (I-2b: 13.7 g) was dissolved in 100 mL of ethyl acetate and treated with 200 mL of a saturated aqueous sodium bicarbonate solution and di-tert-butyl-carbonate (14.3 g, 65.5 mmol). The reaction mixture was stirred at 50° C. for 2 hours before cooling to room temperature and the aqueous phase extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated to provide the title compound (I-2c).

Workup

  1. temperaturebefore cooling to room temperature
  2. extractionthe aqueous phase extracted with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-162130a25cf34cd090e698c4fcce32d4
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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