Water → N-[(4-Bromophenyl)methyl]-N-(1-oxopentyl)-L-valine

HRID 12594

Reaction equation

HRID 12594 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[C:22](Cl)(=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26].O>C1COCC1>[Br:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]([C:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26])[C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 61186Valeryl chlorideHCID 516892Sodium BicarbonateHCID 11673643(S)-2-(4-bromobenzyl)amino-3-methylbutyric acid

Product 1

HCID 11696368N-[(4-Bromophenyl)methyl]-N-(1-oxopentyl)-L-valineYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture made up of 5 g (17.47 mmol) of N-(4-bromobenzyl)-L-valine and 5.9 g (70.24 mmol) of sodium bicarbonate in 50 mL of dry THF is left under stirring and under nitrogen atmosphere for one hour. The preceding suspension is cooled to 0° C. and to it is added over a period of 15 min. 4.2 mL (35.41 mmol) of valeroyl chloride. The mixture is then left to react at 20-25° C. for 3 h, 50 mL of water is added and the THF is distilled at low pressure. The resulting solution is taken to pH 2 with HCl 35% and the remains of THF distilled off completely. The solid obtained is filtered, washed with 50 mL of water and dried in a vacuum over to provide 5.9 g (91.2%) of N-(4-bromobenzyl)-N-valeryl-L-valine. The solid is recrystallised from a mixture of EtOH/H2O 2:1. M.p.=123° C.

Workup

  1. waitis left
  2. additionis added over a period of 15 min
  3. waitThe mixture is then left
  4. customto react at 20-25° C. for 3 h
  5. distillationthe THF is distilled at low pressure
  6. distillationthe remains of THF distilled off completely
  7. customThe solid obtained
  8. filtrationis filtered
  9. washwashed with 50 mL of water
  10. customdried in a vacuum over

Sources & evidence

ORD record
ord-e01ec6a0314544228d23b8e21d159f26
Source dataset
uspto-grants-2010_06
Patent number
US07728021B2

Linked notes

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