1,3-Propanedithiol → Benzyl 4-amino-3-hydroxyazepane-1-carboxylate

HRID 460404ノート

反応式

HRID 460404 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]=[N+]=[N-])[CH:13]([OH:21])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(S)CCS>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH:14]([NH2:18])[CH:13]([OH:21])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 80131,3-PropanedithiolHCID 8471TriethylamineHCID 10661164Benzyl 4-azido-3-hydroxyazepane-1-carboxylate

生成物 1

HCID 10659264Benzyl 4-amino-3-hydroxyazepane-1-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 4-azido-3-hydroxy-azepane-1-carboxylic acid benzyl ester (3.3 g, 11.37 mmol) in methanol (50 mL) was added triethylamine (5 mL) and 1,3-propanedithiol (3.42 mL, 35 mmol). The mixture was stirred at ambient temperature until TLC analysis showed complete consumption of the starting material. A white precipitate was removed by filtration and the filtrate was evaporated to dryness. The residue was triturated with a 1:1 hexane/diethyl ether mixture to remove excess dithiol and dried under vacuum to yield 4-amino-3-hydroxy-azepane-1-carboxylic acid benzyl ester.

後処理

  1. customconsumption of the starting material
  2. customA white precipitate was removed by filtration
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was triturated with a 1:1 hexane/diethyl ether mixture
  5. customto remove excess dithiol
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-3ba44c8eb7d64e09bba35f63be2f0fad
出典データセット
uspto-grants-2007_03
特許番号
US07196099B2

反応ノート

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