1-Hydroxybenzotriazole → HCID 66811749, compound

HRID 1099212Notes

Reaction equation

HRID 1099212 reaction equation
[Cl-].[CH2:2]([N:6]1[CH2:11][CH2:10][N:9]([CH:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([NH:15][NH3+:16])=[O:14])[C:8](=[O:23])[C:7]1=[O:24])[CH2:3][CH2:4][CH3:5].[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH2:35][CH:34]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:33]1[C:44](O)=[O:45])=[O:31])([CH3:28])([CH3:27])[CH3:26].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>ClCCCl>[CH2:2]([N:6]1[CH2:11][CH2:10][N:9]([CH:12]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:13]([NH:15][NH:16][C:44]([CH:33]2[CH:34]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:35][CH2:36][CH2:37][N:32]2[C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])=[O:45])=[O:14])[C:8](=[O:23])[C:7]1=[O:24])[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 450739411-(tert-Butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acidHCID 66811239HCID 66811239, compound

Product 1

HCID 66811749HCID 66811749, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-[(4-butyl-2,3-dioxopiperazin-1-yl)(phenyl)acetyl]hydrazinium chloride (94.0 mg, 0.27 mmol) in 1,2-dichloroethane (2 ml) were added 1-(tert-butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid (71.0 mg, 0.23 mmol), 1-hydroxybenzotriazole (44.5 mg, 0.26 mmol), diisopropylethylamine (0.050 ml, 0.27 mmol), and polystyrene bound carbodiimide (353 mg, 0.46 mmol, 1.34 mmol/g). The reaction was allowed to stir gently at room temperature for 24 h. The reaction was filtered, concentrated, and purified via reverse phase HPLC to yield tert-butyl 2-({2-[(4-butyl-2,3-dioxopiperazin-1-yl)(phenyl)acetyl]hydrazino}carbonyl)-3-phenylpiperidine-1-carboxylate (11%).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-e4a6da5e04434e6cad74dac473d5ef0a
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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