Water → N-Boc-beta-alanine Propargyl Amide

HRID 12007

Reaction equation

HRID 12007 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([NH2:17])C#C.C(N=C=NC(C)C)(C)C.O>C1COCC1>[C:11]([NH2:17])(=[O:13])[C:10]#[CH:9].[C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 12734DiisopropylcarbodiimideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 239041Propargylamine

Product 1

HCID 87766044N-Boc-beta-alanine Propargyl Amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Boc-β-alanine (1a) (1.05 g, 5.5 mmol) and propargyl amine (0.90 g, 16.5 mmol) were dissolved in THF (10 mL). Diisopropyl-carbodiimide (DIC, 695 g, 5.5 mmol) was added and the reaction mixture was stirred for 16 h at room temperature. Water was added (20 mL) and the product was extracted into EtOAc (3×30 mL). The combined EtOAc was dried (Na2SO4) and evaporated. The crude product was purified by silica column chromatography eluting with EtOAc:Heptane gradient (2:3)-(3:2.5) (v/v). Product yield 0.925 g, 74%.

Workup

  1. extractionthe product was extracted into EtOAc (3×30 mL)
  2. dry with materialThe combined EtOAc was dried (Na2SO4)
  3. customevaporated
  4. customThe crude product was purified by silica column chromatography
  5. washeluting with EtOAc

Sources & evidence

ORD record
ord-81c8b3c0439348328e900f92313d677b
Source dataset
uspto-grants-2010_06
Patent number
US07727713B2

Linked notes

Loading…