Triethylamine → N-(2,2-Dimethoxyethyl)biotinamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of D-(+)-biotin 2-nitrophenyl ester (365 mg, 1.00 mmol) in MeCN (20 mL) was added aminoacetaldehyde dimethyl acetal (130 μL, 1.20 mmol) and Et3N (170 μL, 1.20 mmol). The suspension was gently heated until a solution was obtained; the solution was then stirred for 16 h at ˜25° C. The reaction mixture was evaporated to dryness under reduced pressure and the material left was purified by silica gel chromatography using a gradient of MeOH (0→10%) in CH2Cl2 as the eluent. Fractions containing the product were collected and evaporated to dryness under low pressure affording 9 (300 mg, 910 μmol) as a solid in a yield of 91%. 1H NMR (300 MHz, DMSO-d6): δ 7.87 (t, J=5.8 Hz, 1H), 6.43 (s, 1H), 6.37 (s, 1H), 4.32 (t, J=5.5 Hz, 1H), 4.28 (d, J=5.5 Hz, 1H), 4.12 (ddd, J=7.6, 4.4, 1.8 Hz, 1H), 3.25 (s, 6H), 3.13 (t, J=5.7 Hz, 2H), 2.82 (dd, J=12.3, 12.3 Hz, 1H), 2.56 (d, J=12.3 Hz, 1H), 2.07 (t, J=7.4 Hz, 2H), 1.66-1.22 (m, 7H). 13C NMR (75 MHz, DMSO-d6): δ 172.2, 162.6, 102.0, 61.0, 59.1, 55.4, 53.1, 40.2, 39.8, 34.9, 28.1, 28.0, 25.2. +ESI-HRMS: Calcd for C14H25N3O4S [M+H]+ 332.1639. found 332.1641.

Provenance & Evidence