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1,1'-Carbonyldiimidazole → HCID 10853285、化合物

HRID 2393104
ノート
印刷プレビュー

反応式

HRID 2393104 の反応式
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]([O:17][C:18]([NH:20][C@@H:21]([C:25]([OH:27])=O)[CH:22]([CH3:24])[CH3:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(C(C)C)CC)(C)C.[CH2:37]([O:44][NH2:45])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl>[CH3:24][CH:22]([CH3:23])[C@@H:21]([NH:20][C:18](=[O:19])[O:17][C:13]([CH3:14])([CH3:15])[CH3:16])[C:25]([NH:45][O:44][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 102313O-BenzylhydroxylamineHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acid

生成物 1

HCID 10853285HCID 10853285、化合物収率 91%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

CDI (2.45 g, 15.1 mmol) is added to a solution of N-(tert-butoxycarbonyl)-D-valine (3.28 g, 15.1 mmol) and CH2Cl2 (60 mL). The solution is stirred for 1 hour at room temperature. Diisopropylethylamine (2.90 mL, 16.6 mmol) and O-benzylhydroxylamine (2.64 g, 16.5 mmol) are added and the solution stirred for 16 hours at room temperature. The solution is concentrated, diluted with EtOAc, and washed with 5% HCl (2×50 mL), NaHCO3 (50 mL) and brine (50 mL). The organic solution is dried (MgSO4), filtered, and concentrated to give 4.42 g (91%) of the title compound as a white solid which is carried on crude.

後処理

  1. stirringthe solution stirred for 16 hours at room temperature
  2. concentrationThe solution is concentrated
  3. additiondiluted with EtOAc
  4. washwashed with 5% HCl (2×50 mL), NaHCO3 (50 mL) and brine (50 mL)
  5. dry with materialThe organic solution is dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-b703a5ba778f4e989d12e299aa085327
出典データセット
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05804593

反応ノート

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