Sodium Bicarbonate → [(3R,4R,7R)-3-Hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-yl]-carbamic acid tert-butyl ester

HRID 229841Notes

Reaction equation

HRID 229841 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7](Cl)(=[O:9])=[O:8].[C:11]([O:15][C:16](=[O:27])[NH:17][C@@H:18]1[CH2:24][CH2:23][C@@H:22]([CH3:25])[NH:21][CH2:20][C@H:19]1[OH:26])([CH3:14])([CH3:13])[CH3:12].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.CCOC(C)=O>[C:11]([O:15][C:16](=[O:27])[NH:17][C@@H:18]1[CH2:24][CH2:23][C@@H:22]([CH3:25])[N:21]([S:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)(=[O:9])=[O:8])[CH2:20][C@H:19]1[OH:26])([CH3:13])([CH3:12])[CH3:14]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 68998497((3R,4R,7R)-3-Hydroxy-7-methyl-azepan-4-yl)-carbamic acid tert-butyl ester

Product 1

HCID 69000299[(3R,4R,7R)-3-Hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-yl]-carbamic acid tert-butyl esterYield 65.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridine-2-sulfonyl chloride (0.55 g, 3.1 mmol) was added to a solution ((3R,4R,7R)-3-Hydroxy-7-methyl-azepan-4-yl)-carbamic acid tert-butyl ester (0.58 g, 0.2.4 mmol), sodium bicarbonate (0.84 g, 10 mmol) in CH2Cl2 (10 ml) and H2O (3 ml) and was stirred at RT for 30 minutes. The reaction mixture was diluted with EtOAc (100 ml), washed with H2O, brine, dried with magnesium sulfate, filtered, concentrated in vacuo by rotary evaporation, and chromatographed (silica gel, 45:55 EtOAC/hexanes) to yield the title compound (0.6 g, 65%): Electrospray mass spec: M+H+=386.27.

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo by rotary evaporation
  5. customchromatographed (silica gel, 45:55 EtOAC/hexanes)

Sources & evidence

ORD record
ord-827656930ce645a5a4b7dc1ed134bcb8
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Reaction notes

Loading…