4-Methyl-1-pentanol → HCID 86758028, compound

HRID 1934387Notes

Reaction equation

HRID 1934387 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([NH:26][C@H:27]([C:32]#[CH:33])[CH2:28][C:29]([OH:31])=[O:30])=[O:25])[CH2:19]2)=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][CH:35]([CH3:40])[CH2:36][CH2:37][CH2:38]O.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:38]([O:30][C:29](=[O:31])[CH2:28][C@@H:27]([C:32]#[CH:33])[NH:26][C:24]([C@@H:20]1[CH2:21][CH2:22][CH2:23][N:18]([C:16](=[O:17])[CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:12]2)[CH2:19]1)=[O:25])[CH2:37][CH2:36][CH:35]([CH3:40])[CH3:34]

Participants

5

Reactant 3

HCID 122964-Methyl-1-pentanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86757999HCID 86757999, compound

Product 1

HCID 86758028HCID 86758028, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl]-3-piperidylcarbonyl]-3(S)-ethynyl-β-alanine (0.5 g), 4-methyl-1-pentanol 0.15 ml) and N,N-dimethylaminopyridine (13 mg) in dichloromethane (5 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.23 g) at 0° C. After stirring at an ambient temperature overnight, the solution was evaporated in vacuo. The residue was poured into water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate, water and brine, dried over magnesium sulfate, and evaporated in vacuo, subsequently. The residue was purified by column chromatography on silica gel eluting with CHCl3:MeOH (100:1) to give N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl]-3-piperidylcarbonyl]-3(S)-ethynyl-β-alanine isohexyl ester (0.59 g) as an oil.

Workup

  1. customthe solution was evaporated in vacuo
  2. additionThe residue was poured into water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate, water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with CHCl3:MeOH (100:1)

Sources & evidence

ORD record
ord-a8f5d3277dca42289fea3cf8ce1a58ae
Source dataset
uspto-grants-2002_05
Patent number
US06384028B1

Reaction notes

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