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

HRID 460404노트

반응식

HRID 460404 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3ba44c8eb7d64e09bba35f63be2f0fad
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196099B2

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