Acetic Anhydride → methyl (2S)-2-acetamido-3-(4-iodophenyl)propanoate

HRID 37769Notes

Reaction equation

Cl.[NH2:2][C@@H:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5].[C:16]([O-])(=[O:18])[CH3:17].[Na+].C(OC(=O)C)(=O)C>Cl>[C:16]([NH:2][C@@H:3]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([I:15])=[CH:13][CH:14]=1)[C:4]([O:6][CH3:7])=[O:5])(=[O:18])[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 93 (2.25 g, 6.80 mmol) in 10% HCl (10 mL) at 0° C. was added 4M sodium acetate (115 mL) and the resulting reaction was allowed to stir whilst equilibrating to 0° C. Acetic anhydride (50 mL) was added and the reaction allowed to proceed with vigorous stirring. After 1 h the product was collected by vacuum filtration, dissolved in ethyl acetate (30 mL) and washed with 2M sodium bicarbonate (2×30 mL). The organic layer was dried and evaporated to yield the title compound (1.31 g, 3.79 mmol, 56%) as a white solid. Mp 118-120° C. [α]D)27+93.8 (c. 0.1, CHCl3). 1H NMR (CDCl3, 300 MHz): δ 7.61 (d, J=8.4 Hz, 2H, ArH2′ and ArH6′); 6.84 (d, J=8.1 Hz, 2H, ArH3′ and ArH5′); 5.92 (d, J=7.2 Hz, 1H, NH); 4.87 (m, 1H, H2); 3.73 (s, 3H, OCH3); 3.11 (dd, J=6.0, 13.8, Hz, 1H, H3a); 3.03 (dd, J=5.4, 13.8 Hz, 1H, H3b); 1.99 (s, 3H, NCOCH3). Mass Spectrum (CI, +ve) m/z 348 (100%) [MH+]. HRMS calcd for C12H15NO3I 348.0097, found 348.0104.

Workup

customthe resulting reaction
filtrationAfter 1 h the product was collected by vacuum filtration
dissolutiondissolved in ethyl acetate (30 mL)
washwashed with 2M sodium bicarbonate (2×30 mL)
customThe organic layer was dried
customevaporated

Sources & evidence

ORD record: ord-8e3d92c3d8c445248fa0cffae424e5ab
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524657B2

Reaction notes

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