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

反応式

HRID 1796879 の反応式
[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]

参加物

6

反応物 4

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

生成物 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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cf1da0af55b84698803c304c84df7561
出典データセット
uspto-grants-2006_04
特許番号
US07030265B2

関連ノート

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