Sodium Bicarbonate → HCID 69459074, compound

HRID 1351976Notes

Reaction equation

HRID 1351976 reaction equation
[CH3:1][C@@H:2]([N:24]([CH2:32][C@@H:33]([C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1)[O:34][Si](CC)(CC)CC)C(=O)OC(C)(C)C)[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([O:13][C@H:14]([CH3:23])[C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.Cl.O1CCOCC1.C(=O)([O-])O.[Na+]>C(O)C>[CH3:1][C@@H:2]([NH:24][CH2:32][C@@H:33]([C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1)[OH:34])[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([O:13][C@H:14]([CH3:23])[C:15]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[O:16])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 86604030HCID 86604030, compound

Product 1

HCID 69459074HCID 69459074, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Further, to a solution of tert-butyl (1R)-1-methyl-2-(7-(((1R)-1-methyl-2-morpholin-4-yl-2-oxoethyl)oxy)-1H-indol-3-yl)ethyl((2R)-2-pyridin-3-yl-2-((triethylsilyl)oxy)ethyl)carbamate (190 mg, 0.285 mmol) in ethanol (2.0 mL) is added a 4N hydrochloric acid/dioxane (2.0 mL, 8.0 mmol), and the mixture is stirred at room temperature for 14 hours. To the reaction solution are added a saturated aqueous sodium hydrogen carbonate solution and a saturated brine, and the mixture is extracted with chloroform, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (a saturated ammonia solution in chloroform/methanol=100/1→100/4) to give the title compound (107 mg, yield: 83%).

Workup

  1. extractiona saturated brine, and the mixture is extracted with chloroform
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue is purified by silica gel column chromatography (a saturated ammonia solution in chloroform/methanol=100/1→100/4)

Sources & evidence

ORD record
ord-e4fd7c6ad0e041ad964bfc380ba66a9e
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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