(+-)-Methionine → 2-[6-[(3-Hydroxyphenyl)methyl]-1-cyclohexen-1-yl]-4,5-diphenyloxazole

HRID 377304Notes

Reaction equation

HRID 377304 reaction equation
O[C:2]1([C:17]2[O:18][C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:21]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15]C)[CH:10]=1.NC(C(O)=O)CCSC>CS(O)(=O)=O>[OH:15][C:11]1[CH:10]=[C:9]([CH2:8][CH:3]2[C:2]([C:17]3[O:18][C:19]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[C:20]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:21]=3)=[CH:7][CH2:6][CH2:5][CH2:4]2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 876(+-)-Methionine2×HCID 184591732-[(1RS,2SR)-1-hydroxy-2-[(3-methoxyphenyl)methyl]cyclohexyl]-4,5-diphenyloxazole

Product 1

HCID 193584952-[6-[(3-Hydroxyphenyl)methyl]-1-cyclohexen-1-yl]-4,5-diphenyloxazoleYield 43.4%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

A suspension of 2-[(1RS,2SR)-1-hydroxy-2-[(3-methoxyphenyl)methyl]cyclohexyl]-4,5-diphenyloxazole (2.23 g) and DL-methionine (7.56 g) in methanesulfonic acid (33.0 ml) was stirred at 60° C. for 17 hours, then another DL-methionine (7.56 g) and methanesulfonic acid (33.0 ml) was added thereto. The mixture was stirred at the same temperature for 23 hours and poured into ice-water. The resulting aqueous mixture was extracted three times with ethyl acetate. The extracts were combined, washed with sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (n-hexane-diethyl ether (100:20)) over silica gel. The first eluate afforded 2-[6-[(3-hydroxyphenyl)methyl]-1-cyclohexen-1-yl]-4,5-diphenyloxazole (897 mg) as paste.

Workup

  1. stirringThe mixture was stirred at the same temperature for 23 hours
  2. extractionThe resulting aqueous mixture was extracted three times with ethyl acetate
  3. washwashed with sodium bicarbonate aqueous solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed (n-hexane-diethyl ether (100:20)) over silica gel

Sources & evidence

ORD record
ord-4d8096b761aa47e481649b1e3dc289da
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

Loading…