Acetic Anhydride → HCID 5102925, compound

HRID 1158365Notes

Reaction equation

HRID 1158365 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[NH2:15][C:16]([CH3:22])([CH3:21])[CH2:17][C:18]([OH:20])=[O:19].CCOC(C)=O>CN(C1C=CN=CC=1)C.C1COCC1>[C:8]([NH:15][C:16]([CH3:22])([CH3:21])[CH2:17][C:18]([OH:20])=[O:19])(=[O:10])[CH3:9]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 27609333-Amino-3-methylbutanoic acid

Product 1

HCID 5102925HCID 5102925, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (1.8 mL, 12.8 mmol), acetic anhydride (1.2 mL, 12.8 mL) and DMAP (10 mg, 0.09 mmol) are subsequentially added to a suspension of 3-amino-3-methyl-butyric acid (1.00 g, 8.5 mmol) in THF (100 mL). After heating at 60° C. for 3 h AcOEt is added and the organic phase is washed with 1N HCl. Drying (Na2SO4), filtration and evaporation of the solvent yields the desired product. MS (LC-MS): [M+H]+=160.1. tR (HPLC, Waters Symmetry C18 column, 20-95% CH3CN/H2O/3.5 min, 95% CH3CN/H2O, 2 min, CH3CN and H2O containing 0.1% TFA, flow: 0.6 mL/min): 0.40 min.

Workup

  1. additionis added
  2. washthe organic phase is washed with 1N HCl
  3. customDrying
  4. filtration(Na2SO4), filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-dfee4e0c4e674d188a38af8b7e7d6161
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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