(2S,5S)-2,5-dimethylpiperazine → N,N-diethyl-4-(3-(tert-butyldimethylsilyloxy)-alpha-((2S,5S)-2,5-dimethyl-1-piperazinyl)benzyl)benzamide

HRID 1460086

Reaction equation

HRID 1460086 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([CH:11](Cl)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:13]=2)=[CH:7][CH:6]=1)[CH3:2].[CH3:30][C@H:31]1[CH2:36][NH:35][C@@H:34]([CH3:37])[CH2:33][NH:32]1.N[C@H](C(N[C@H](C(O)=O)C)=O)C.O=C1NCCNC1=O>C1(C)C=CC=CC=1>[CH2:1]([N:3]([CH2:28][CH3:29])[C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([N:32]2[CH2:33][C@H:34]([CH3:37])[NH:35][CH2:36][C@@H:31]2[CH3:30])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:13]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 61380(2S,5S)-2,5-dimethylpiperazineHCID 223500364-(3-(tert-butyldimethylsilyloxy)-alpha-chlorobenzyl)-N,N-diethylbenzamideHCID 131720131L-Ala-L-Ala diketopiperazine

Product 1

HCID 22940840N,N-diethyl-4-(3-(tert-butyldimethylsilyloxy)-alpha-((2S,5S)-2,5-dimethyl-1-piperazinyl)benzyl)benzamideYield 22.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 15.65 g (36 mmol) of N,N-diethyl-4-(3-(t-butyldimethylsilyloxy)-α-chlorobenzyl)benzamide, prepared as described in Example 11, 7.22 g (65 mmol) of (+)-(2S,5S)-2,5-dimethylpiperazine, prepared from L-Ala-L-Ala-diketopiperazine (Bachem Chemicals, Philadelphia, Pa.) as described by Jung and Rohloff (J. Org. Chem. 50, 4909-13 (1985)), and 3 mL of toluene was heated as in Example 1. The product was purified by chromatography on silica gel (Waters Prep 500 with dichloromethane containing 1% ethanol and 0.1% triethylamine) to give 4.06 g (22%) of N,N-diethyl-4-(3-(tert-butyldimethylsilyloxy)-α-((2S,5S)-2.5-dimethyl-1-piperazinyl)benzyl)benzamide as a beige foam.

Workup

  1. customprepared
  2. temperaturewas heated as in Example 1
  3. customThe product was purified by chromatography on silica gel (Waters Prep 500 with dichloromethane containing 1% ethanol and 0.1% triethylamine)

Sources & evidence

ORD record
ord-164e355ecd3b43879fde3bb9d55bff59
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Linked notes

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