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Guanidine → tert-butyl (2S)-3-[4-(4-carbamimidamido-4-oxobutoxy)phenyl]-2-(phenylmethoxycarbonylamino)propanoate

HRID 2184947
ノート
印刷プレビュー

反応式

HRID 2184947 の反応式
[NH2:1][C:2]([NH2:4])=[NH:3].[CH2:5]([O:12][C:13]([NH:15][C@@H:16]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][C:35](OCC)=[O:36])=[CH:27][CH:26]=1)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)(C)(C)C.C1COCC1>[CH2:5]([O:12][C:13]([NH:15][C@@H:16]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][C:35]([NH:3][C:2]([NH2:4])=[NH:1])=[O:36])=[CH:27][CH:26]=1)[C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])=[O:14])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 3520Guanidine2 回HCID 11038228tert-Butyl (2S)-2-benzyloxycarbonylamino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate

生成物 1

HCID 178451190tert-butyl (2S)-3-[4-(4-carbamimidamido-4-oxobutoxy)phenyl]-2-(phenylmethoxycarbonylamino)propanoate収率 42%

試薬・触媒・溶媒 2

HCID 6386tert-Butanol溶媒2 回
HCID 8028
Tetrahydrofuran
溶媒

実験手順

A solution of 3.64 g (61.69 mmol) of guanidine in 150 ml of tert-butanol was added to a solution of 20 g (41.23 mmol) of (1.1) in THF and the mixture was stirred at room temperature for 18 h. A further 4.5 g of guanidine in 150 ml of tert-butanol were then added, and the reaction solution was stirred at room temperature for 7 h, concentrated to about a half and stirred at room temperature for a further 18 h. The solvent was removed in vacuo and the residue was first filtered through basic Al2O3 using CH2Cl2/MeOH/H2O (95/5/0.5) and then chromatographed on silica gel by means of MPLC using CH2Cl2/MeOH/acetic acid (90/10/0.5). 8.6 g (42%) of (1.2) were obtained.

後処理

  1. stirringthe reaction solution was stirred at room temperature for 7 h
  2. concentrationconcentrated to about a half
  3. stirringstirred at room temperature for a further 18 h
  4. customThe solvent was removed in vacuo
  5. filtrationthe residue was first filtered through basic Al2O3
  6. customchromatographed on silica gel by means of MPLC

出典と根拠

ORDレコード
ord-54ccd8a338674e0ebc135f78d36cad75
出典データセット
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06399620B1

反応ノート

読み込み中…

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