N-(Prop-2-yn-1-yl)methanesulfonamide → 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(4-(methyl sulfonamidomethyl)-1H-1,2,3-triazol-1-yl)phenyl) propan-2-yl) acetamide

Participants

Role	Name	HCID	Charge
Reactant	N-(Prop-2-yn-1-yl)methanesulfonamide	HCID 14025440	—
Reactant	N-[(1S,2R)-2-(4-Azido-phenyl)-1-fluoromethyl-2-hydroxy-ethyl]-2,2-dichloro-acetamide	HCID 86695459	—
Product	2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(4-(methyl sulfonamidomethyl)-1H-1,2,3-triazol-1-yl)phenyl) propan-2-yl) acetamide	HCID 89790578	—

Reaction Steps

Following the general procedure of Example 66, Step 3 and making non-critical variations but using the product of step 1, Example 67 with the product of Example 66, Step 2 the title compound is obtained (45 mg). 1H-NMR (400 MHz, DMSO-d6) δ: 2.95 (s, 3H), 4.25-4.26 (m, 1H), 4.30 (s, 2H), 4.33-4.34 (m, 0.5H), 4.42-4.46 (m, 0.5H), 4.58-4.61 (m, 0.5H), 4.69-4.73 (m, 0.5H), 4.95 (t, 1H, J=3.3 Hz), 6.08 (d, 1H, J=3.92 Hz), 6.49 (s, 1H), 7.55 (d, 2H, J=8.56 Hz), 7.84 (d, 2H, J=8.6 Hz), 8.64 (d, 1H, J=9.04 Hz), 8.70 (s, 1H). LC-MS (m/z): [M+H]=453.9.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09428528B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-0d3af132544c4132a950a295bf2edaed
Source note	uspto-grants-2016_08