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

HRID 377304ノート

反応式

HRID 377304 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6395Methanesulfonic Acid溶媒2 回

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4d8096b761aa47e481649b1e3dc289da
出典データセット
uspto-grants-2000_02
特許番号
US06025375

反応ノート

読み込み中…