Sodium Bicarbonate → HCID 90051731, compound

HRID 2284684Notes

Reaction equation

HRID 2284684 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH:29]=O)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(OCC)(=O)C.C(O)(=O)C>[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][NH:15][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 3268011tert-Butyl (2-aminocyclohexyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 10398106Benzyl (3-Oxopropyl)carbamate

Product 1

HCID 90051731HCID 90051731, compoundYield 107.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-1,2-cyclohexanediamine (200 mg) and 3-((benzyloxycarbonyl)amino)propionaldehyde (65 mg) in methylene chloride (4 mL), sodium triacetoxyborohydride (133 mg) and acetic acid (18 μL) were added at room temperature, and the mixture was stirred at the same temperature for 5 hours and 30 minutes. To the reaction mixture, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then 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 0% hexane in ethyl acetate) to obtain tert-butyl (2-((3-((benzyloxycarbonyl)amino)propyl)amino)cyclohexyl)carbamate (C39, 137 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-a6033559b0444393b40bf4a442f46938
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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