Dichloromethane → HCID 69457286, compound

HRID 1351958Notes

Reaction equation

HRID 1351958 reaction equation
C(N(CC)C([CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[C:12]2[CH2:16][CH2:17][NH:18][C@@H:19]([CH3:29])[C@H:20]([OH:28])[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)=O)C.P([O-])([O-])(O)=O.[Na+].[Na+].F[B-](F)(F)F.[CH2:44]([O+:46](CC)CC)[CH3:45].C(Cl)Cl.C(=O)([O-])[OH:55].[Na+]>C(#N)C>[OH:28][C@H:20]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[C@@H:19]([NH:18][CH2:17][CH2:16][C:12]1[C:11]2[C:15](=[C:7]([C:6]([O:46][CH2:44][CH3:45])=[O:55])[CH:8]=[CH:9][CH:10]=2)[NH:14][CH:13]=1)[CH3:29]

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 24203Sodium Phosphate, DibasicHCID 516892Sodium Bicarbonate2×HCID 2723982Triethyloxonium tetrafluoroborateHCID 131726448HCID 131726448, compound

Product 1

HCID 69457286HCID 69457286, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N,N-diethyl-3-(2-(((1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl)amino)ethyl)-1H-indole-7-carboxyamide (215.5 mg, 0.526 mmol) in acetonitrile (18 mL) is added disodium hydrogen phosphate (112 mg, 0.789 mmol) under nitrogen atmosphere, and thereto is further added a 1N solution of triethyloxonium tetra-fluoroborate in methylene chloride (1.58 mL, 1.58 mmol), and the mixture is stirred at room temperature for 15 hours. To the reaction solution are added a saturated aqueous sodium hydrogen carbonate solution (18 mL) and sodium hydrogen carbonate (200 mg), and the mixture is further stirred for 2 hours. The mixture is separated into water and chloroform, and the organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. The solvent is evaporated, and the obtained crude product is purified by silica gel column chromatography (chloroform: methanol=50:1 5:1) to give ethyl 3-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-(methyl) ethylamino]ethyl}-1H-indole-7-carboxylate (128.4 mg, 0.336 mmol, 64%).

Workup

  1. stirringthe mixture is further stirred for 2 hours
  2. customThe mixture is separated into water and chloroform
  3. washthe organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is evaporated
  6. customthe obtained crude product
  7. customis purified by silica gel column chromatography (chloroform: methanol=50:1 5:1)

Sources & evidence

ORD record
ord-3bf2f7aa71ab4bbfb9f0b615afc1d092
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

Loading…