Sodium Chloride → HCID 90052135, compound

HRID 2284744Notes

Reaction equation

HRID 2284744 reaction equation
[NH2:1][CH2:2][C:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH2:8][CH2:9][O:10][CH3:11])[CH2:4][CH2:5][O:6][CH3:7].C(=O)([O-])O.[Na+].[C:25](=O)([O:41]N1C(=O)CCC1=O)[O:26][CH2:27][CH:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2.[Cl-].[Na+]>O1CCOCC1.O.C(OCC)(=O)C>[CH3:11][O:10][CH2:9][CH2:8][C:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])([CH2:4][CH2:5][O:6][CH3:7])[CH2:2][NH:1][C:25](=[O:41])[O:26][CH2:27][CH:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516892Sodium BicarbonateHCID 90052284HCID 90052284, compound

Product 1

HCID 90052135HCID 90052135, compoundYield 69.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of tert-butyl (3-(aminomethyl)-1,5-dimethoxypentan-3-yl)carbamate (G21, 275 mg) and sodium hydrogencarbonate (400 mg) in 1,4-dioxane (4 mL) and water (4 mL), 9-fluorenylmethyl succinimidyl carbonate (261 mg) was added under ice cooling, and the mixture was stirred at the same temperature for 2 hours, and then stirred at room temperature for 1 hour. To the reaction mixture, ethyl acetate and saturated aqueous sodium chloride were added. The organic layer was separated, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 30% hexane in ethyl acetate) to obtain (9H-fluoren-9-yl)methyl tert-butyl (4-methoxy-2-(2-methoxyethyl)butane-1,2-diyl)dicarbamate (G22, 269 mg).

Workup

  1. additionwas added under ice cooling
  2. stirringstirred at room temperature for 1 hour
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 30% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-af5993c227224eae8c4aa9a01a610839
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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