Sodium Bicarbonate → HCID 67313552, compound

HRID 1010881Notes

Reaction equation

HRID 1010881 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH2:23]([O:30][C:31](=[O:41])[N:32]([CH2:34][C:35](N(OC)C)=[O:36])[CH3:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:23]([O:30][C:31](=[O:41])[N:32]([CH2:34][C:35]([C:13]1[CH:14]=[CH:15][C:10]([C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17])[CH3:9])=[CH:11][CH:12]=1)=[O:36])[CH3:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 56973617(S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamateHCID 86625210HCID 86625210, compoundHCID 178418339Butyllithium

Product 1

HCID 67313552HCID 67313552, compoundYield 12.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

200 mg of the compound [1-1] was dissolved in 4 mL of tetrahydrofuran, and the mixture was cooled to −78° C. and then 626 μL of n-butyllithium (2.66 M hexane solution) was added thereto. After a 1 hour stirring at the same temperature, 0.6 mL of tetrahydrofuran solution containing 177 mg of the compound [2-1] was added thereto, and the mixture was further stirred for 2 hours. To the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=6/4), to obtain 36.2 mg of benzyl[2-(4-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}phenyl)-2-oxoethyl]methylcarbamate [2-2] (hereinafter, referred to as the compound [2-2]) as a colorless oily product.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe resulting organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insolubles were filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=6/4)

Sources & evidence

ORD record
ord-c07d319c480f47ae942c2aa3366d6b13
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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