Ammonium Hydroxide → HCID 23363621, compound

HRID 1081252Notes

Reaction equation

HRID 1081252 reaction equation
[CH2:1]([CH:4]([CH2:14][CH2:15][CH3:16])[C:5]([NH:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=O)=[O:6])[CH2:2][CH3:3].[NH4+:17].[OH-:18]>O1CCOCC1>[CH2:1]([CH:4]([CH2:14][CH2:15][CH3:16])[C:5]([NH:7][C:8](=[O:18])[CH2:9][CH2:10][CH2:11][NH2:17])=[O:6])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 23363625HCID 23363625, compound

Product 1

HCID 23363621HCID 23363621, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To an ice-cooled solution of N-(2-propylpentanoyl)-4-aminobutyroyl chloride (prepared from N-(2-propylpentanoyl)-4-aminobutyric acid and SOC12, 5.9 g, 24.0 mmole) in dioxane (25 ml), was added dropwise conc. NH4OH (34 ml) over 1 hr. The reaction mixture was then stirred at RT for 20 hrs and evaporated to dryness under reduced pressure. The residue was taken up in an H2O (20 ml) and EtOAC (30 ml) mixture, the mixture stirred vigorously for 5 min. The organic phase was separated, evaporated to dryness under reduced pressure, and the residue crystallized from EtOAc to give 1.4 g (6.1 mmole, 26%) of a crystalline solid, mp 138° C.

Workup

  1. customevaporated to dryness under reduced pressure
  2. stirringthe mixture stirred vigorously for 5 min
  3. customThe organic phase was separated
  4. customevaporated to dryness under reduced pressure
  5. customthe residue crystallized from EtOAc

Sources & evidence

ORD record
ord-f92b10f718a747269b6210e9dbb5b6ce
Source dataset
uspto-grants-1996_12
Patent number
US05585358

Reaction notes

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