2-Methylpropyl(4-(3,6-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]carbamate → 2-Methylpropyl[3-fluoro-4-(tetrahydro-1,1-dioxido-2h-thiopyran-4-yl)phenyl]carbamate

HRID 1979069Notes

Reaction equation

HRID 1979069 reaction equation
[H][H].[CH3:3][CH:4]([CH3:25])[CH2:5][O:6][C:7](=[O:24])[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH2:16][CH2:17][S:18](=[O:22])(=[O:21])[CH2:19][CH:20]=2)=[C:11]([F:23])[CH:10]=1>>[CH3:3][CH:4]([CH3:25])[CH2:5][O:6][C:7](=[O:24])[NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][S:18](=[O:22])(=[O:21])[CH2:17][CH2:16]2)=[C:11]([F:23])[CH:10]=1

Participants

3

Reactant 2

HCID 696930012-Methylpropyl(4-(3,6-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 695447062-Methylpropyl[3-fluoro-4-(tetrahydro-1,1-dioxido-2h-thiopyran-4-yl)phenyl]carbamate

Procedure

Following the general procedure of EXAMPLE 4 (and using knowledge known to those skilled in the art regarding reduction of unsaturated cyclic double bonds with hydrogen) and making non-critical variations but starting with 2-methylpropyl[4-(3,6-dihydro-1,1-ioxido-2H-thiopyran-4-yl)-3-fluorophenyl]carbamate (XV, EXAMPLE 12), the title compound is obtained, TLC Rf=0.73 (methanol/methylene chloride, 5/95); mp=181-182°;NMR (CDCl3) δ 7.36, 7.13, 7.01, 6.87, 3.95, 3.33-3.05, 2.42-2.33, 2.18, 2.01-1.94 and 0.96; CMR (CDCl3) δ 159.5, 153.5, 138.4, 127.3, 124.3, 114.2, 106.2, 71.5, 51.5, 34.4, 30.1, 27.9 and 18.9; MS (CI, NH3) m/z (relative intensity) 361 (100), 343 (30), 344 (10), 251(10), 243 (7) and 151(22).

Sources & evidence

ORD record
ord-322734571c68414b9496b5e359b8edec
Source dataset
uspto-grants-2001_05
Patent number
US06239283B1

Reaction notes

Loading…