(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol → HCID 69595763, compound

HRID 1794127Notes

Reaction equation

HRID 1794127 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([F:11])[C:3]=1[CH2:4][OH:5].[CH3:12][C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]=1[CH2:24]O.Cl[C:27]([N:29]1[C@H:34]([CH3:35])[CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][C@@H:30]1[CH3:43])=[O:28]>>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:24][C:14]2[C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:16][O:17][C:13]=2[CH3:12])[CH:7]=[C:6]([F:11])[C:3]=1[CH2:4][O:5][C:27]([N:29]1[C@H:34]([CH3:35])[CH2:33][NH:32][CH2:31][C@@H:30]1[CH3:43])=[O:28]

Participants

4

Reactant 3

HCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanolHCID 222199753,5-Difluoro-4-(hydroxymethyl)phenolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 69595763HCID 69595763, compound

Procedure

cis-2,6-Dimethyl-piperazine-1-carboxylic acid 2,6-difluoro-4-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-benzyl ester was prepared from 2,6-difluoro-4-hydroxybenzyl alcohol, (5-methyl-3-phenyl-isoxazol-4-yl)-methanol and 1-chlorocarbonyl-cis-2,6-dimethyl-4-tert-butoxycarbonylpiperazine according to the procedures described for Example 54 and 121 to give the product as a yellow oil: δH (400 MHz; d6-DMSO) 1.15 (6H, d, J 7.0 Hz), 2.53 (3H, s), 2.62 (2H, dd, J 12.0, 4.5 Hz), 2.68 (2H, d, J 12.0 Hz), 3.80–3.88 (2H, m), 5.01–5.08 (4H, m), 6.84–6.91 (2H, m), 7.48–7.53 (3H, m) and 7.64–7.68 (2H, m).

Sources & evidence

ORD record
ord-4ff256885a5149308af15242f4dcf20f
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

Loading…