1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 131723563, compound

HRID 1297200Notes

Reaction equation

HRID 1297200 reaction equation
[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:2]([C:5]([OH:7])=O)([CH3:4])[CH3:3].Cl.C(N=C=NCCCN(C)C)C.[NH2:27][C@@H:28]([C:39]([N:41]1[CH2:48][CH2:47][CH2:46][C@@H:42]1[C:43]([OH:45])=[O:44])=[O:40])[CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:32][CH:31]=1.[CH2:49]([N-:53][CH2:54][CH:55]([CH3:57])[CH3:56])[CH:50]([CH3:52])[CH3:51]>C(Cl)Cl>[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:2]([C:5]([NH:27][C@@H:28]([C:39]([N:41]1[CH2:48][CH2:47][CH2:46][C@@H:42]1[C:43]([OH:45])=[O:44])=[O:40])[CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:32][CH:31]=1)=[O:7])([CH3:3])[CH3:4].[CH2:49]([N-:53][CH2:54][CH:55]([CH3:57])[CH3:56])[CH:50]([CH3:52])[CH3:51]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 131723561HCID 131723561, compound

Product 1

HCID 131723563HCID 131723563, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In a 100 ml round bottom flask, 0.50 mmol of Boc-Aib (Aib=α-aminoisobutyric acid) was dissolved in 30 ml dry CH2Cl2 and then 0.51 mmol of 1-hydroxybenzotrizole was added while stirring under N2 atmosphere in an ice-bath, 0.55 mmol of 1-ethyl-3-(3′-dimethylaminopropyl) carbodiimide HCl was added in 20 ml dry CH2Cl2 at a fast drop rate and the reaction was stirred for 1 hour at 0° C. 0.51 mmol of (2) in 15 ml of CH2Cl2 was added dropwise and stirring was continued for a further 18 h at ambient temperature. The reaction mixture was washed with 20 ml of 20% citric acid aqueous solution, 20 ml of saturated NaCHO3 aqueous solution, and 20 ml of saturated sodium chloride aqueous solution. The organic layer was separated and dried over anhydrous magnesium sulfate, filtered and concentrated in vacuum. Further purification was done by flash column chromatography (CHCl3/MeOH, 95:5) to afford white solid of Boc-Aib-DTrp-DPro-diisobutylamide.

Workup

  1. addition0.51 mmol of 1-hydroxybenzotrizole was added
  2. stirringthe reaction was stirred for 1 hour at 0° C
  3. stirringstirring
  4. washThe reaction mixture was washed with 20 ml of 20% citric acid aqueous solution, 20 ml of saturated NaCHO3 aqueous solution, and 20 ml of saturated sodium chloride aqueous solution
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. customFurther purification

Sources & evidence

ORD record
ord-7964204833e0497d99745b6ad01a8075
Source dataset
uspto-grants-2007_07
Patent number
US07250399B2

Reaction notes

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