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

HRID 460404Notes

Reaction equation

HRID 460404 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3ba44c8eb7d64e09bba35f63be2f0fad
Source dataset
uspto-grants-2007_03
Patent number
US07196099B2

Reaction notes

Loading…