Sodium Hydroxide → HCID 67178573, compound

HRID 1807918Notes

Reaction equation

HRID 1807918 reaction equation
[CH3:1][C:2]([CH3:18])([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][CH:4]1[NH:8]C(=O)N[C:5]1=[O:10].[OH-:19].[Na+]>>[NH2:8][CH:4]([CH2:3][C:2]([CH3:18])([CH3:1])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:19])=[O:10]

Participants

3

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 67177917HCID 67177917, compound

Product 1

HCID 67178573HCID 67178573, compound

Conditions

Temperature
120 °C

Procedure

A suspension of (RS)-5-(2,2-dimethyl-3-phenyl-propyl)-imidazolidine-2,4-dione (2.04 g) in 4 N NaOH was heated under an argon atmosphere to 120° C. (oil bath temperature). After 30 min strong foaming was observed. More 4 N NaOH (20 ml) was added. The suspension was heated to 120° C. for 2 days, turning into a clear solution. The mixture was cooled to r.t. and the insoluble material was filtered off The filtrate was cooled in an ice bath and concentrated HCl was carefully added until pH ˜6 was reached. The solid that had precipitated out was collected by filtration, washed with plenty of H2O and with Et2O, and dried to give (RS)-2-amino-4,4-dimethyl-5-phenyl-pentanoic acid (5.39 g, product contains large amount of salt) as white solid which was used in the next step without further purification.

Workup

  1. temperatureThe suspension was heated to 120° C. for 2 days
  2. temperatureThe mixture was cooled to r.t.
  3. filtrationthe insoluble material was filtered off The filtrate
  4. temperaturewas cooled in an ice bath
  5. additionconcentrated HCl was carefully added until pH ˜6
  6. customThe solid that had precipitated out
  7. filtrationwas collected by filtration
  8. washwashed with plenty of H2O and with Et2O
  9. customdried

Sources & evidence

ORD record
ord-8aee642a79264bcb9344d3054d2e436b
Source dataset
uspto-grants-2013_01
Patent number
US08357712B2

Reaction notes

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