Sodium Bicarbonate → HCID 131728998, compound

HRID 1010878Notes

Reaction equation

HRID 1010878 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])=[CH:8][CH:7]=1)=[O:5].[Na].C(=O)([O-])O.[Na+]>CO>[C:17]([O:16][C:15](=[O:21])[NH:14][C@H:12]([C:9]1[CH:8]=[CH:7][C:6]([CH:4]([OH:5])[CH2:3][N:2]([CH3:1])[CH3:22])=[CH:11][CH:10]=1)[CH3:13])([CH3:19])([CH3:18])[CH3:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 131728999HCID 131728999, compound

Product 1

HCID 131728998HCID 131728998, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

26.3 mg of the compound [1-4] was dissolved in 1.5 mL of methanol, 16.2 mg of sodium boronhydride was added thereto, and the mixture was stirred for 30 minutes at room temperature. To the reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate, and the solution was extracted with a mixed solvent of chloroform and methanol (mixing ratio: 9/1). The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The insolubles were filtered, and the filtrate was concentrated under reduced pressure, to obtain tert-butyl((1S)-1-{4-[2-(dimethylamino)-1-hydroxyethyl]phenyl}ethyl)carbamate [1-5] (hereinafter, referred to as the compound [1-5]). The compound [1-5] was used in the subsequent reaction without further purification.

Workup

  1. extractionthe solution was extracted with a mixed solvent of chloroform and methanol (mixing ratio: 9/1)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insolubles were filtered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a87d6801813c4a53b029b16742300428
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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