Diisopropylethylamine → C20-Otbu-glu(otbu)-aeea-aeea-osu

HRID 2361848ノート

反応式

HRID 2361848 の反応式
[C:1]([O:5][C:6](=[O:61])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:60])[NH:26][C@H:27]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:28][CH2:29][C:30](=[O:52])[NH:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][C:39](=[O:51])[NH:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][C:48]([OH:50])=[O:49])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CN(C(O[N:75]1[C:80](=[O:81])[CH2:79][CH2:78][C:76]1=[O:77])=[N+](C)C)C.CCN(C(C)C)C(C)C>C(#N)C>[C:1]([O:5][C:6](=[O:61])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:60])[NH:26][C@H:27]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:28][CH2:29][C:30](=[O:52])[NH:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][C:39](=[O:51])[NH:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][C:48]([O:50][N:75]1[C:80](=[O:81])[CH2:79][CH2:78][C:76]1=[O:77])=[O:49])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 86644529(S)-22-(tert-Butoxycarbonyl)-45,45-dimethyl-10,19,24,43-tetraoxo-3,6,12,15,44-pentaoxa-9,18,23-triazahexatetracontanoic acid

生成物 1

HCID 86644531C20-Otbu-glu(otbu)-aeea-aeea-osu収率 99%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 19-{(S)-1-tert-Butoxycarbonyl-3-[2-(2-{[2-(2-carboxymethoxyethoxy)ethylcarbamoyl]-methoxy}ethoxy)ethylcarbamoyl]propylcarbamoyl}nonadecanoic acid tert-butyl ester (3.1 g) in acetonitrile (50 ml) was added TSTU (1.39 g) and DIPEA (0.91 ml). The mixture was stirred at room temperature over night and then concentrated in vacuo. To the residue was added aqueous 0.1 N HCl (100 ml) and ethyl acetate (200 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate (50 ml). The combined organic layers were washed with water and brine, dried (magnesium sulphate) and concentrated in vacuo to give an oil. Yield 99% (3.4 g). LC-MS (electrospray): m/z: 971.8.

後処理

  1. concentrationconcentrated in vacuo
  2. additionTo the residue was added aqueous 0.1 N HCl (100 ml) and ethyl acetate (200 ml)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (50 ml)
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried (magnesium sulphate)
  7. concentrationconcentrated in vacuo
  8. customto give an oil

出典と根拠

ORDレコード
ord-f1d721c9103245fda9baf2c414cf47b5
出典データセット
uspto-grants-2014_04
特許番号
US08691759B2

反応ノート

読み込み中…