Triethylamine → N-(4-(2-(hydroxy)ethyl)phenyl)pent-4-ynamide

HRID 879904Notes

Reaction equation

HRID 879904 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH2:3][C:4]#[CH:5].[OH:8]N1C(=O)CCC1=O.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23](O)[CH3:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[OH:8][CH2:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 857534-Amino-alpha-methylbenzenemethanolHCID 86640145N-hydroxysuccinimide-(4-pentynoate)

Product 1

HCID 58427477N-(4-(2-(hydroxy)ethyl)phenyl)pent-4-ynamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

N-hydroxysuccinimide-(4-pentynoate) (Ref: Malkoch, M.; Schleicher, K.; Drockenmuller, E.; Hawker, C. J.; Russell, T. P.; Wu, P.; Fokin, V. V., Structurally Diverse Dendritic Libraries: A Highly Efficient Functionalization Approach Using Click Chemistry. Macromolecules 2005, 38, (9), 3663-3678.) (200 mg, 1.0 mmol) and p-aminophenylethanol (125 mg, 0.9 mmol) were dissolved in 2 mL of dichloromethane together with triethyl amine (140 μL, 1.0 mmol), and 5 drops of dimethyl formamide. The reaction mixture was stirred at room temperature for 2 hours. The crude reaction product was concentrated, dissolved in 10 mL of ethyl acetate and washed with 5 mL of water followed by, 5 mL of 0.5 M HCl (aq.), 5 mL of 10 NaHCO3 (aq.) and finally 5 mL of water. The organic phase was dried with MgSO4, filtered, and the solvent was evaporated. The product was further purified by column chromatography on silica gel eluting with a gradient of toluene (T) and ethyl acetate (E) from 4:1 to 1:2 (T:E). The product N-(4-(2-(hydroxy)ethyl)phenyl)pent-4-ynamide was characterized by NMR and MALDI-TOF.

Workup

  1. customThe crude reaction product
  2. concentrationwas concentrated
  3. dissolutiondissolved in 10 mL of ethyl acetate
  4. washwashed with 5 mL of water
  5. dry with materialThe organic phase was dried with MgSO4
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe product was further purified by column chromatography on silica gel eluting with a gradient of toluene (T) and ethyl acetate (E) from 4:1 to 1:2 (T:E)

Sources & evidence

ORD record
ord-73e91c8ec3984de1a56dc5003152c6a8
Source dataset
uspto-grants-2015_03
Patent number
US08992963B2

Reaction notes

Loading…