Triethylamine → HCID 58010777, compound

HRID 2079270Notes

Reaction equation

HRID 2079270 reaction equation
[OH:1][C@H:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([OH:5])=O.[CH2:10]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([C:3](=[O:5])[C@H:2]([OH:1])[CH2:6][CH:7]([CH3:9])[CH3:8])[CH2:19][CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 759941-BenzylpiperazineHCID 439960(R)-2-hydroxy-4-methylpentanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 58010777HCID 58010777, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (0-5° C.) of (R)-α-hydroxyisocaproic acid (64.5 g, 0.5 mol), 1-benzylpiperazine (88 g, 0.5 mol) and triethylamine (71 ml, 0.5 mol) in CH2Cl2 (850 ml) was added in portions HOBt (68 g, 0.5 mol) and EDCI.HCl (96 g, 0.5 mol). The reaction mixture was stirred at room temperature overnight. The organic layer was washed with water (3×) and once with brine, dried over Na2SO4, and filtered, and the solvent was removed in vacuo. Crude (R)-1-(4-benzyl-piperazin-1-yl)-2-hydroxy-4-methyl-pentan-1-one (132 g, 91%) was used in the next step without further purification.

Workup

  1. washThe organic layer was washed with water (3×) and once with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customCrude (R)-1-(4-benzyl-piperazin-1-yl)-2-hydroxy-4-methyl-pentan-1-one (132 g, 91%) was used in the next step without further purification

Sources & evidence

ORD record
ord-5f0cf55606b84d3d81740580a6584128
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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