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Hydrochloric Acid → (S)-2-{[1-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carbonyl]-amino}-4-methyl-pentanoic acid tert-butyl ester

HRID 1750165
ノート
印刷プレビュー

反応式

HRID 1750165 の反応式
[CH2:1]([CH:3]([N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15](O)=[O:16])=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][O:20]1)[CH2:4][CH3:5])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[C:44]([O:48][C:49](=[O:56])[C@H:50]([CH2:52][CH:53]([CH3:55])[CH3:54])[NH2:51])([CH3:47])([CH3:46])[CH3:45].Cl>CN(C=O)C.O.C(Cl)CCl>[C:44]([O:48][C:49](=[O:56])[C@@H:50]([NH:51][C:15]([C:13]1[CH:12]=[CH:11][C:10]2[N:6]([CH:3]([CH2:1][CH3:2])[CH2:4][CH3:5])[C:7]([CH2:18][CH:19]3[CH2:23][CH2:22][CH2:21][O:20]3)=[N:8][C:9]=2[CH:14]=1)=[O:16])[CH2:52][CH:53]([CH3:54])[CH3:55])([CH3:46])([CH3:45])[CH3:47]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2 回HCID 12451443tert-butyl (2S)-2-amino-4-methylpentanoate hydrochlorideHCID 867143751-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carboxylic acid

生成物 1

HCID 86714374
(S)-2-{[1-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carbonyl]-amino}-4-methyl-pentanoic acid tert-butyl ester
収率 88.8%

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 55 mg of 1-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carboxylic acid in 1 ml of dry DMF 26 mg of HOBT, 37 mg of EDC and 0.05 ml of DIPEA were added at 0° C. After 15 min 100 mg of L-leucine tert-butyl ester-hydrochloride and 0.05 ml of DIPEA were added and the reaction was stirred at rt for 16 h. The reaction was then poured into water and the pH was adjusted to 3 by the addition of 2 M aqueous hydrochloric acid. The reaction was extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and concentrated. 75 mg (88%) of (S)-2-{[1-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carbonyl]-amino}-4-methyl-pentanoic acid tert-butyl ester were obtained.

後処理

  1. extractionThe reaction was extracted with ethyl acetate three times
  2. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-e192452960a240c29cc578b5538b690e
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09156796B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート