Hydrochloric Acid → HCID 13491570, compound

HRID 567654Notes

Reaction equation

HRID 567654 reaction equation
[NH2:1][CH:2]([C:7]([OH:9])=[O:8])[C:3]([CH3:6])([CH3:5])[CH3:4].[C:10]1([CH2:16][C:17](Cl)=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>[OH-].[Na+]>[C:10]1([CH2:16][C:17]([NH:1][CH:2]([C:7]([OH:9])=[O:8])[C:3]([CH3:6])([CH3:5])[CH3:4])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 3061312-Amino-3,3-dimethylbutanoic acid

Product 1

HCID 13491570HCID 13491570, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of DL-tert-leucine (2 g, 15.3 mol) in aqueous sodium hydroxide (2 M, 25 ml) was added dropwise phenylacetyl chloride (646 mg, 20.8 mmol), simultaneously with sodium hydroxide (2 M, 25 ml), at 0° C. over a period of 5 min. The solution was allowed to warm to room temperature and stirred for an additional 60 min until complete dissolution occurred. The reaction was then cooled to 0° C., acidified to pH 4 with conc. HCl, and stirred for 30 min. The resulting precipitate was collected by filtration, dried, and recrystallised from ethanol/water (1:1 v/v) to yield the product as a white solid (2.06 g, 54%).

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. stirringstirred for 30 min
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried
  5. customrecrystallised from ethanol/water (1:1 v/v)

Sources & evidence

ORD record
ord-bb694dd8020e444c94344b7ae9b06d39
Source dataset
uspto-grants-2001_01
Patent number
US06180374B2

Reaction notes

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