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

HRID 1487513

Reaction equation

HRID 1487513 reaction equation
[CH2:1]([NH:4][S:5]([CH3:8])(=[O:7])=[O:6])[C:2]#[CH:3].[N:9]([C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]([OH:28])[C@H:19]([NH:22][C:23](=[O:27])[CH:24]([Cl:26])[Cl:25])[CH2:20][F:21])=[CH:14][CH:13]=1)=[N+:10]=[N-:11]>>[Cl:25][CH:24]([Cl:26])[C:23]([NH:22][C@H:19]([CH2:20][F:21])[C@H:18]([OH:28])[C:15]1[CH:14]=[CH:13][C:12]([N:9]2[CH:3]=[C:2]([CH2:1][NH:4][S:5]([CH3:8])(=[O:7])=[O:6])[N:11]=[N:10]2)=[CH:17][CH:16]=1)=[O:27]

Participants

3

Reactant 2

HCID 14025440N-(Prop-2-yn-1-yl)methanesulfonamideHCID 86695459N-[(1S,2R)-2-(4-Azido-phenyl)-1-fluoromethyl-2-hydroxy-ethyl]-2,2-dichloro-acetamide

Product 1

HCID 897905782,2-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

Procedure

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.

Sources & evidence

ORD record
ord-0d3af132544c4132a950a295bf2edaed
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Linked notes

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