(1R,3R,4S,5S)-3-amino-5-[3-fluoro-4-nitro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol hydrochloride → (1R,3S,4S,5R)-3-[4-Amino-3-fluoro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-5-[3-(1-methyl-cyclopropyl)-benzylamino]-1-oxo-tetrahydro-thiopyran-4-ol

Participants

Reaction Steps

The title compound can be prepared in an analogous manner as described for example 41 steps c) and d) from (1R,3R,4S,5S)-3-amino-5-[3-fluoro-4-nitro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol hydrochloride and 3-(1-methyl-cyclopropyl)benzaldehyde to yield the title compound as a yellowish foam: TLC (CH2Cl2-MeOH 9:1) Rf=0.48; HPLC RtG3=1.70 min; ESIMS [M+H]+=559.3; 1H NMR (400 MHz, DMSO-d6): δ 7.22-7.18 (m, 2H), 7.11 (d, 1H), 7.07 (d, 1H), 6.72 (s, 1H), 6.64 (d, 1H), 5.09 (m, 1H), 4.99 (d, 1H), 4.58 (s, 2H), 3.75 (m, 3H), 3.59 (d, 1H), 3.32 (s, 3H), 3.19-3.09 (m, 3H), 2.98 (m, 1H), 2.69 (m, 1H), 2.45-2.25 (m, 4H), 1.36 (s, 3H), 0.83 (m, 2H), 0.72 (m, 2H).

Provenance & Evidence