Dichloromethane → Di[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenyl](2S)-2-[(tert-butoxycarbonyl)amino]butanedioate

HRID 1796879

반응식

HRID 1796879 반응식
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][C:11]([OH:13])=[O:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)Cl.Cl.C(N=C=N[CH2:26][CH2:27][CH2:28]N(C)C)C.[CH3:32][C:33]1[CH2:38][CH2:37][CH2:36][C:35]([CH3:40])([CH3:39])[C:34]=1/[CH:41]=[CH:42]/[C:43](/[CH3:52])=[CH:44]/[CH:45]=[CH:46]/[C:47](/[CH3:51])=[CH:48]/[CH2:49]O>CN(C)C=O>[CH3:51]/[C:47](/[CH:46]=[CH:45]/[CH:44]=[C:27](\[CH3:26])/[CH:28]=[CH:41]/[C:34]1[C:35]([CH3:39])([CH3:40])[CH2:36][CH2:37][CH2:38][C:33]=1[CH3:32])=[CH:48]\[CH2:49][O:15][C:14](=[O:16])[C@@H:9]([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:10][C:11]([O:13][CH2:49]/[CH:48]=[C:47](\[CH3:51])/[CH:46]=[CH:45]/[CH:44]=[C:43](\[CH3:52])/[CH:42]=[CH:41]/[C:34]1[C:35]([CH3:40])([CH3:39])[CH2:36][CH2:37][CH2:38][C:33]=1[CH3:32])=[O:12]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 99718N-(tert-butoxycarbonyl)-L-aspartic acidHCID 445354RetinolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 86590977Di[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenyl](2S)-2-[(tert-butoxycarbonyl)amino]butanedioate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

N-Boc aspartic acid (1.2 mg), methylene chloride 20 ml and minimum amount of dimethylformamide (DMF) were added to nitrogen filled, three mouth- round bottom flask and melted. The reaction mixture was cooled down into 0° C., 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride [EDCI](1.36 g)were added slowly, and stirred for approximately 30 minutes. Retinol (0.51 g) was added into the reaction mixture, small amount of N,N′-dimethylaminopyridine (DMAP) were added immediately, and stirred for approximately 1˜3 hours. After the reaction was finished, eluent were removed under the low pressure, the residues were melted with ethyl acetate and washed several times with water and Brine. Organic phase were dried with anhydrous MgSO4, concentrated under low pressure and separated with column chromatography.

후처리

  1. additionfilled
  2. additionwere added immediately
  3. stirringstirred for approximately 1˜3 hours
  4. customeluent were removed under the low pressure
  5. washwashed several times with water and Brine
  6. dry with materialOrganic phase were dried with anhydrous MgSO4
  7. concentrationconcentrated under low pressure
  8. customseparated with column chromatography

출처 및 근거

ORD 기록
ord-cf1da0af55b84698803c304c84df7561
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030265B2

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