Sodium Carbonate → N-Boc-beta-n-butyl-alpha,alpha-dimethyl-beta-alanine

HRID 361763Notes

Reaction equation

HRID 361763 reaction equation
Cl.[CH2:2]([CH:6]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=[O:10])[NH2:7])[CH2:3][CH2:4][CH3:5].C(=O)([O-])[O-].[Na+].[Na+].[C:20]([O:24][C:25](=O)[O:26]C(C)(C)C)([CH3:23])([CH3:22])[CH3:21]>O1CCOCC1>[C:25]([NH:7][CH:6]([CH2:2][CH2:3][CH2:4][CH3:5])[C:8]([CH3:12])([CH3:13])[C:9]([OH:11])=[O:10])([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 86753676beta-n-Butyl-alpha,alpha-dimethyl-beta-alanine hydrochloride

Product 1

HCID 10778649N-Boc-beta-n-butyl-alpha,alpha-dimethyl-beta-alanineYield 66.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

β-n-butyl-α,α-dimethyl-β-alanine hydrochloride (3.65 g, 17.40 mmol) was dissolved into 10% aqueous sodium carbonate (18.4 ml). To the resulting solution was added dioxane solution (50 ml) of di-t-butylcarbonate (4.6 g, 20.87 mmol) under cooling with ice and stirred at room temperature overnight. The solvent was distilled off and the resulting residue was dissolved into water, washed with ether and adjusted to pH 3 with citric acid under cooling with ice, followed by the several times of ethyl acetate extraction. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate. The solvent were removed in vacuo, and recrystallized from ether-hexane mixed solvent to give crystal of N-Boc-β-n-butyl-α,α-dimethyl-β-alanine (3.16 g, 66.4%).

Workup

  1. temperatureunder cooling with ice
  2. distillationThe solvent was distilled off
  3. dissolutionthe resulting residue was dissolved into water
  4. washwashed with ether
  5. temperatureunder cooling with ice
  6. extractionfollowed by the several times of ethyl acetate extraction
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent were removed in vacuo
  10. customrecrystallized from ether-hexane mixed solvent

Sources & evidence

ORD record
ord-e7633202670743b9abcb3716624ad2bc
Source dataset
uspto-grants-1999_02
Patent number
US05866592

Reaction notes

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