Benzenamine, 3-ethynyl- → HCID 90052292, compound

HRID 2284747Notes

Reaction equation

HRID 2284747 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])#[CH:2].[C:10]([NH:17][CH2:18][CH:19]=O)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(Cl)Cl.C(O)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:6][CH2:19][CH2:18][NH:17][C:10](=[O:11])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1)#[CH:2]

Participants

8

Reactant 4

HCID 104682Benzenamine, 3-ethynyl-HCID 516892Sodium BicarbonateHCID 4247255tert-butyl N-(2-oxoethyl)carbamate2×HCID 5049666Sodium triacetoxyborohydride2×

Product 1

HCID 90052292HCID 90052292, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 3-ethynylaniline (100 mg) and N-Boc-2-aminoacetaldehyde (407 mg) in ethyl acetate (5 mL) and methylene chloride (5 mL), acetic acid (2 drops) and sodium triacetoxyborohydride (543 mg) were added at room temperature, and the mixture was stirred at the same temperature for 3 hours and 30 minutes. To the reaction mixture, N-Boc-2-aminoacetaldehyde (200 mg) and sodium triacetoxyborohydride (200 mg) were added at room temperature, and the mixture was stirred at the same temperature. To the reaction mixture, saturated aqueous sodium hydrogencarbonate and ethyl acetate 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 basic silica gel column chromatography (eluent, 75% hexane/25% ethyl acetate) to obtain tert-butyl (2-((3-ethynylphenyl)amino)ethyl)carbamate (G27).

Workup

  1. stirringthe mixture was stirred at the same temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography (eluent, 75% hexane/25% ethyl acetate)

Sources & evidence

ORD record
ord-397c137f7ad84925887a90874b73a51d
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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