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

HRID 377304노트

반응식

HRID 377304 반응식
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

참가 물질

4

반응물 2

HCID 876(+-)-Methionine2회HCID 184591732-[(1RS,2SR)-1-hydroxy-2-[(3-methoxyphenyl)methyl]cyclohexyl]-4,5-diphenyloxazole

생성물 1

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

시약·촉매·용매 1

HCID 6395Methanesulfonic Acid용매2회

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d8096b761aa47e481649b1e3dc289da
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06025375

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