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Ethanol → ethyl 2-amino-5-(4-benzyloxyphenyl)-1H-pyrrole-3-carboxylate

HRID 853283
ノート
印刷プレビュー

反応式

HRID 853283 の反応式
C(O)C.Cl.[C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[NH:7])[NH2:6].[O-]CC.[Na+].[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=O)[CH2:33]Br)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[CH2:12]([O:11][C:9]([C:8]1[CH:33]=[C:32]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:27][CH:28]=2)[NH:7][C:5]=1[NH2:6])=[O:10])[CH3:13]
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 702EthanolHCID 2723922Sodium ethoxideHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-oneHCID 15555354Ethyl 2-carbamimidoylacetate hydrochloride

生成物 1

HCID 22936919ethyl 2-amino-5-(4-benzyloxyphenyl)-1H-pyrrole-3-carboxylate収率 103.1%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

実験手順

After adding 700 ml of ethanol to 50.7 g of ethyl 2-amidinoacetate hydrochloride (a publicly known compound described in Liebigs Ann. Chem., 1895 (1977)), the mixture was stirred at room temperature, 22.3 g of sodium ethoxide (1 equivalent with respect to ethyl 2-amidinoacetate hydrochloride) was added, and the mixture was stirred for 15 minutes under a nitrogen atmosphere. To this there was added 49.9 g of 1-(4-benzyloxyphenyl)-2-bromoethanone (publicly known compound described in Journal of Heterocyclic Chemistry, vol.2, 310 (1965) and Journal of Medicinal Chemistry, vol.17, 55 (1974)), and the mixture was stirred for 36 hours at room temperature under a nitrogen atmosphere. Water was added, ethyl acetate was used for liquid separation and extraction, and then the organic layer was dried over sodium sulfate and concentrated to dryness to obtain 56.7 g of the title compound.

後処理

  1. stirringthe mixture was stirred for 15 minutes under a nitrogen atmosphere
  2. stirringwas stirred for 36 hours at room temperature under a nitrogen atmosphere
  3. customethyl acetate was used for liquid separation and extraction
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-d1aa5fb4325741f8b10006cf0ad37168
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07253286B2

反応ノート

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