1-Hydroxybenzotriazole → HCID 131723571, compound

HRID 1297204Notes

Reaction equation

HRID 1297204 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].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[NH2:37][C@@H:38]([C:49]([N:51]1[CH2:58][CH2:57][CH2:56][C@@H:52]1[C:53]([OH:55])=[O:54])=[O:50])[CH2:39][C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[NH:42][CH:41]=1.CC1CCCN(C(N)=O)C1>C(Cl)Cl>[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:2]([C:5]([NH:37][C@@H:38]([C:49]([N:51]1[CH2:58][CH2:57][CH2:56][C@@H:52]1[C:53]([OH:55])=[O:54])=[O:50])[CH2:39][C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[NH:42][CH:41]=1)=[O:7])([CH3:3])[CH3:4].[NH:42]1[CH2:41][CH2:40][CH2:39][CH:38]([C:49]([NH2:51])=[O:50])[CH2:43]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 131723569HCID 131723569, compound

Product 1

HCID 131723571HCID 131723571, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In a 50 ml round bottom flask, 0.33 mmol of Boc-Aib was dissolved in 20 ml dry CH2Cl2 and then 0.31 mmol of 1-hydroxybenzotriazole was added while stirring under N2 atmosphere in an ice-bath. 0.35 mmol of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide HCL was added in 10 ml dry CH2Cl2 at a fast drop rate and the reaction mixture was stirred for 1 hour at 0° C. 0.30 mmol of (2) in 15 ml of CH2Cl2 was added dropwise and stirring was continued for an additional 18 h at ambient temperature. The reaction mixture was washed with ml of 20% citric acid aqueous solution, 20 ml of saturated NaHCO3 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-3-piperidinamide.

Workup

  1. stirringthe reaction mixture was stirred for 1 hour at 0° C
  2. stirringstirring
  3. washThe reaction mixture was washed with ml of 20% citric acid aqueous solution, 20 ml of saturated NaHCO3 aqueous solution and 20 ml of saturated sodium chloride aqueous solution
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customFurther purification

Sources & evidence

ORD record
ord-f8e7c1af6db247ad8b82e788df5e885f
Source dataset
uspto-grants-2007_07
Patent number
US07250399B2

Reaction notes

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