Acetic Anhydride → HCID 22225456, compound

HRID 2223236Notes

Reaction equation

HRID 2223236 reaction equation
C(O[NH:9][CH2:10][CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:12]([OH:14])=[O:13])C1C=CC=CC=1.[C:20]([O:23][C:24](=O)[CH3:25])(=[O:22])C>C(O)=O.ClCCl>[CH2:24]([O:23][C:20]([NH:9][CH2:10][CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:12]([OH:14])=[O:13])=[O:22])[C:25]1[CH:17]=[CH:16][CH:15]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 22225525HCID 22225525, compound

Product 1

HCID 22225456HCID 22225456, compoundYield 199.2%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold solution of 2-(benzyloxyaminomethyl)heptanoic acid (1.57 g, 5.92 mmol) in HCO2H (29 mL) and dichloromethane (29 mL) was added acetic anhydride (5.9 mL, 62.75 mmol) at 0° C. The mixture was stirred at 0° C. for 3 hours. The volatiles were removed by evaporation under vacuum. Dichloromethane (50 mL) was added to the residue, and the solution was washed with brine, and dried over MgSO4. Filtration and evaporation under vacuum provided the title compound (1.73 g, 100%). 1H NMR (400 MHz, CHCl3) δ 8.07 (br s, 1H), 7.29 (m, 5H), 4.91–4.71 (m, 2H), 3.76 (m, 2H), 2.67 (m, 1H), 1.54 (m, 1H), 1.41(m, 1H), 1.20 (m, 6H), 0.80 (t, J=7.0 Hz, 3H). MH+ 294.

Workup

  1. customThe volatiles were removed by evaporation under vacuum
  2. additionDichloromethane (50 mL) was added to the residue
  3. washthe solution was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and evaporation under vacuum

Sources & evidence

ORD record
ord-52ae0f90f8934b4aaab83dbe022cdc0a
Source dataset
uspto-grants-2008_05
Patent number
US07375120B2

Reaction notes

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