1-Hydroxybenzotriazole → HCID 89806721, compound

HRID 1474586Notes

Reaction equation

HRID 1474586 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[CH2:10][C@@H:11]([C:20]([OH:22])=O)[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([CH:30]([NH2:34])[CH2:31][CH2:32][CH3:33])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH2:1]([O:8][C:9](=[O:23])[CH2:10][C@@H:11]([C:20]([NH:34][CH:30]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:31][CH2:32][CH3:33])=[O:22])[NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1581888N-tert-Butoxycarbonyl-L-aspartic acid beta-benzyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 36037851-phenylbutan-1-amine

Product 1

HCID 89806721HCID 89806721, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4.27 g of N-(tert-butoxycarbonyl)aspartic acid-4-benzyl ester (manufactured by PEPTIDE INSTITUTE, INC.) and 2.1 mL of 1-phenylbutyl amine were dissolved in 40 mL of DMF, and then 2.70 g of WSC hydrochloride and 1.93 g of HOBt were added thereto, and the reaction solution was stirred at room temperature for 6 hours. The reaction solution was added with water, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried with magnesium sulfate, and then distilled under reduced pressure to remove ethyl acetate, and then dried under vacuum, thereby to give 3.94 g of Compound 1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialdried with magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove ethyl acetate
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c71d2fb91c394f708315971f9fdad084
Source dataset
uspto-grants-2015_04
Patent number
US09018323B2

Reaction notes

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