1-Hydroxybenzotriazole → HCID 69839741, compound

HRID 1836132Notes

Reaction equation

HRID 1836132 reaction equation
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][CH:5]=[C:4]([CH2:11][CH2:12][C:13]([OH:15])=O)[C:3]1=2.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[N:35]1([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>ClCCl>[C:44]([O:43][C:41]([N:35]1[CH2:40][CH2:39][N:38]([C:13](=[O:15])[CH2:12][CH2:11][C:4]2[C:3]3[C:2](=[O:1])[CH2:10][CH2:9][CH2:8][C:7]=3[NH:6][CH:5]=2)[CH2:37][CH2:36]1)=[O:42])([CH3:47])([CH3:45])[CH3:46]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 158327213-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoic acid

Product 1

HCID 69839741HCID 69839741, compoundYield 118.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-Oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (2.07 g, 10 mmol), prepared as described in Example 1 above, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide-hydrochloide (2.3 g, 12 mmol), anhydrous 1-hydroxybenzotriazole (1.62 g, 12 mmol) and N,N-diisopropylethylamine (1.75 ml, 10 mmol) were mixed together in 50 ml of dichloromethane and stirred for one hour at room temperature. Tert-butyl 1-piperazinecarboxylate (2.24 g, 12 mmol) was added to the mixture and stirred at room temperature overnight. The reaction mixture was concentrated and the syrup was dissolved in dichloromethane then purified by flash chromatography, eluting with dichloromethane followed by (dichloromethane: methanol 50/1, 30/1) to give 4-[3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionyl]-piperazine-1-carboxylic acid tert-butyl ester (4.45 g, 86% pure).

Workup

  1. stirringstirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe syrup was dissolved in dichloromethane
  4. customthen purified by flash chromatography
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-3de10522cdae432d9eace58677fbc7c4
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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