Hydrochloric Acid → HCID 178447404、化合物

HRID 1590122ノート

反応式

HRID 1590122 の反応式
C[O:2][C:3](=O)[C@H:4]([CH2:34][C:35]1[N:39]=[CH:38][NH:37][CH:36]=1)[NH:5][C:6](=[O:33])[C@H:7]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH:8][C:9](=[O:25])[C@H:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].[BH4-].[Na+].Cl>O1CCCC1.CO>[OH:2][CH2:3][CH:4]([NH:5][C:6](=[O:33])[C@H:7]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[NH:8][C:9](=[O:25])[C@H:10]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:34][C:35]1[N:39]=[CH:38][NH:37][CH:36]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 178501418HCID 178501418、化合物

生成物 1

HCID 178447404HCID 178447404、化合物収率 68.8%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

N-Pivaloyl-L-phenylalanyl-L phenylalanyl-L-histidine methyl ester (1.90 g) is dissolved in tetrahydrofuran (12 ml), and a solution of sodium borohydride (0.20 g) in methanol (2.5 ml) is added dropwise thereto. The mixture is stirred at room temperature for four hours, and 5% hydrochloric acid (4 ml) is added to the mixture and then the solvent is distilled off. The residue is made alkaline with an aqueous sodium bicarbonate solution and then extracted with ethyl acetate. The extract is washed with an aqueous sodium chloride solution, dried, and concentrated to remove solvent. The residue is triturated with ethyl acetate to give 4-{2-hydroxymethyl-2-[N-(N-pivaloyl-L-phenylalanyl-L-phenylalanyl)amino]ethyl}imidazole (1.24 g) as white powder. Yield: 68.8%

後処理

  1. distillationthe solvent is distilled off
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with an aqueous sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customto remove solvent
  7. customThe residue is triturated with ethyl acetate

出典と根拠

ORDレコード
ord-6148a169ed8740b7b04230e0f02b26a3
出典データセット
uspto-grants-1993_04
特許番号
US05202312

反応ノート

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