2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol → HCID 23590006, compound

HRID 898427Notes

Reaction equation

HRID 898427 reaction equation
[OH:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]([CH3:20])([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[CH3:23][C:24]1[O:28][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:26][C:25]=1[CH2:35][CH2:36]O>>[CH3:20][C:7]([O:6][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:36][CH2:35][C:25]2[N:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:28][C:24]=2[CH3:23])=[CH:22][CH:21]=1)([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

3

Reactant 2

HCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanolHCID 12134924HCID 12134924, compound

Product 1

HCID 23590006HCID 23590006, compound

Procedure

Mitsunobu coupling of 2-(4-hydroxyphenoxy)-2-methyl-3-phenylpropionic acid, ethyl ester and 2-(5-methyl-2-phenyloxazol-4-yl)ethanol [Hulin, et al., J. Med. Chem. (1992) 35(10), 1853-64] in the manner described in Example 2, Step A. 1H NMR (300 MHz, CDCl3) δ 7.89-7.93 (m, 2H), 7.33-7.41 (m, 3H), 7.19-7.23 (m, 5H), 6.74 (d, 2H), 6.70 (d, 2H), 4.17 (q, 2H), 4.13 (t, 2H), 3.24 (d, 1H), 3.09 (d, 1H), 2.91 (t, 2H), 2.32 (s, 3H), 1.25 (s, 3H), 1.21 (t, 3H); MS(EI): 486 (M+1).

Sources & evidence

ORD record
ord-a950dac79b254bb796b380cd7bc9149a
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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