Sodium Bicarbonate → HCID 66701241, compound

HRID 2062088Notes

Reaction equation

HRID 2062088 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]([NH:9][C:10]([C:12]1[CH:21]=[C:20]([Cl:22])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O:23][CH2:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:11])([CH3:8])[CH2:6][CH3:7])[CH3:2].[BH-](O[C:42]([CH3:44])=O)(OC(C)=O)OC(C)=O.[Na+].[C:46](=O)([O-])O.[Na+]>ClCCl.CC(O)=O.CC(C)=O>[CH2:1]([O:3][C:4](=[O:31])[C:5]([NH:9][C:10]([C:12]1[CH:21]=[C:20]([Cl:22])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O:23][CH2:24][CH:25]1[CH2:26][CH2:27][N:28]([CH:42]([CH3:44])[CH3:46])[CH2:29][CH2:30]1)=[O:11])([CH3:8])[CH2:6][CH3:7])[CH3:2]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 66701077HCID 66701077, compound

Product 1

HCID 66701241HCID 66701241, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 180AcetoneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 70 mg of 2-{[4-chloro-1-(piperidin-4-yl-methoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-butyric acid ethyl ester (see example 160, step b)) and 9 mg of acetone in 6 mL dichloromethane was added 14 mg HOAc followed by addition of Na(OAc)3BH (46 mg). After 16 hours at room temperature, 9 mg of acetone, 14 mg of HOAc and 46 mg of Na(OAc)3BH were added. The reaction mixture was stirred at room temperature overnight. Aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with dichloromethane. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo. The resulting residue was purified by flash chromatography (silica, 7N NH3 in MeOH/dichloromethane) to give 46 mg of 2-{[4-chloro-1-(1-isopropyl-piperidin-4-ylmethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-butyric acid ethyl ester.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography (silica, 7N NH3 in MeOH/dichloromethane)

Sources & evidence

ORD record
ord-044c4191ca8f4afca543ddd6c7dbc8e1
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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