Triethylamine → Ethyl 2-azido-4-{[1-(tert-butoxycarbonyl)propyl]amino}butanoate

HRID 1765646Notes

Reaction equation

HRID 1765646 reaction equation
[NH2:1][CH:2]([CH2:10][CH3:11])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[N:12]([CH:15]([CH2:21][CH2:22]Br)[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N+:13]=[N-:14].C(N(CC)CC)C>C(#N)C>[N:12]([CH:15]([CH2:21][CH2:22][NH:1][CH:2]([C:3]([O:5][C:6]([CH3:7])([CH3:9])[CH3:8])=[O:4])[CH2:10][CH3:11])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N+:13]=[N-:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13283519tert-Butyl 2-aminobutanoateHCID 22016955Ethyl 2-azido4-bromobutanoate

Product 1

HCID 22017052Ethyl 2-azido-4-{[1-(tert-butoxycarbonyl)propyl]amino}butanoateYield 52.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 2-amino-butanoate (0.397 g) and ethyl 2-azido-4-bromo-butanoate (0.286 g) in acetonitrile (5 ml) was added triethylamine (0.347 ml). The mixture was heated at 50° C. for 18 h, cooled and evaporated onto silica gel (Merck.7734). The pre-absorbed material was purified by flash column chromatography (Merck. 9385, eluting with cyclohexane:ethyl acetate 6:1) to give the title compound (0.200 g) as a mixture of four diastereomers.

Workup

  1. temperaturecooled
  2. customevaporated onto silica gel (Merck.7734)
  3. customThe pre-absorbed material was purified by flash column chromatography (Merck. 9385, eluting with cyclohexane:ethyl acetate 6:1)

Sources & evidence

ORD record
ord-f9700ddb93c24b59a2ca6ae1240cdc60
Source dataset
uspto-grants-2007_06
Patent number
US07226929B2

Reaction notes

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