Acetic Anhydride → (2R)-[(benzyloxyformylamino)methyl]heptanoic acid

HRID 2074972Notes

Reaction equation

C(O[NH:9][CH2:10][C@@H: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][C@@H: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

Conditions

Temperature: 0 °C

Procedure

To a cold solution of (R)-3-benzyloxyamino-2-pentylpropionic acid (1.03 g, 3.89 mmol) in HCO2H (19 mL) and dichloromethane (19 mL) at 0° C. was added acetic anhydride (3.9 mL, 41.2 mmol). The mixture was stirred at 0° C. for 3 hours. The volatiles were removed by evaporation under vacuum. Dichloromethane (50 mL) was added. The organic solution was washed with brine (50 mL×2), and dried over MgSO4. Filtration and evaporation under vacuum provided the title compound (1.08 g, 95%). 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

customThe volatiles were removed by evaporation under vacuum
additionDichloromethane (50 mL) was added
washThe organic solution was washed with brine (50 mL×2)
dry with materialdried over MgSO4
filtrationFiltration and evaporation under vacuum

Sources & evidence

ORD record: ord-dd83941194224ccda26dce17e56da6dc
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919528B2

Reaction notes

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