N-(3-Aminopropyl)morpholine → HCID 23625006, compound

HRID 917301Notes

Reaction equation

HRID 917301 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:20][CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>C1COCC1>[N:24]1([CH2:23][CH2:22][CH2:21][NH:20][C:17](=[O:19])[C@@H:9]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 637610Boc-D-phenylalanine

Product 1

HCID 23625006HCID 23625006, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution in 15 ml of anhydrous THF of tert-butyloxycarbonyl-D-phenylalanine N-hydroxysuccinimmidyl ester (500 mg, 1.38 mmol), N-(3-aminopropyl)-morpholine (1.328 mmol, 0.201 ml) is added. The stirring is maintained for 90 min. The solvent is then evaporated, and the residue dissolved with AcOEt (50 ml); the organic phase is washed with NaHCO3 1M (3×50 ml), HCl 1M (3×50 ml), saturated aqueous solution of sodium chloride (3×50 ml). The solution dried on anhydrous Na2SO4. Following the evaporation of the solvent, 474 mg of (ter-butyloxycarbonyl-D-phenylalanine-N-[3(morpholin-4-yl)propyl]amide) (1.21 mmol, yield=88%) are obtained.

Workup

  1. temperatureThe stirring is maintained for 90 min
  2. customThe solvent is then evaporated
  3. dissolutionthe residue dissolved with AcOEt (50 ml)
  4. washthe organic phase is washed with NaHCO3 1M (3×50 ml), HCl 1M (3×50 ml), saturated aqueous solution of sodium chloride (3×50 ml)
  5. dry with materialThe solution dried on anhydrous Na2SO4

Sources & evidence

ORD record
ord-fbe786b2eaee48e4bfe7e7c62f48ef21
Source dataset
uspto-grants-2007_09
Patent number
US07273856B2

Reaction notes

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