2,2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-hydroxy-2-(4-trimethylstannanyl-phenyl)-ethyl]-acetamide → 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(5-(methylsulfonamidomethyl)-1,3,4-thiadiazol-2-yl)phenyl)propan-2-yl)acetamide

HRID 525515Notes

Reaction equation

HRID 525515 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[N:4][N:3]=1.[Cl:13][CH:14]([Cl:33])[C:15]([NH:17][C@H:18]([CH2:31][F:32])[C@H:19]([OH:30])[C:20]1[CH:25]=[CH:24][C:23]([Sn](C)(C)C)=[CH:22][CH:21]=1)=[O:16]>>[Cl:13][CH:14]([Cl:33])[C:15]([NH:17][C@H:18]([CH2:31][F:32])[C@H:19]([OH:30])[C:20]1[CH:21]=[CH:22][C:23]([C:2]2[S:6][C:5]([CH2:7][NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[N:4][N:3]=2)=[CH:24][CH:25]=1)=[O:16]

Participants

3

Reactant 2

HCID 866953832,2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-hydroxy-2-(4-trimethylstannanyl-phenyl)-ethyl]-acetamideHCID 86695399N-((5-bromo-1,3,4-thiadiazol-2-yl)methyl)methane-sulfonamide

Product 1

HCID 866953982,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(5-(methylsulfonamidomethyl)-1,3,4-thiadiazol-2-yl)phenyl)propan-2-yl)acetamide

Procedure

Following the general procedure of Example 9—Step 2 and making non-critical variations but using N-((5-bromo-1,3,4-thiadiazol-2-yl)methyl)methanesulfonamide and 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(trimethyl-stannyl)phenyl)-propan-2-yl)acetamide the title compound is obtained (11.8 mg): 1H NMR (400 MHz, DMSO-d6) 3.0 (s, 3H), 4.2-4.4 (m, 1.5H), 4.45 (t, 1H), 4.55-4.6 (m, 0.5H), 4.65 (d, 2H), 4.7-4.75 (m, 0.5H), 4.95 (bt, 0.5H), 6.1 (d, 1H), 6.5 (s, 1H), 7.5 (d, 2H), 7.95 (d, 2H), 8.15 (t, 1H), 8.6 (d, 1H). m/z (Cl) M+H 471.

Sources & evidence

ORD record
ord-b368610011074e99bcb9a782e862e4fc
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

Loading…