Sodium Carbonate → 3,3-dimethyl-2-(phenylmethoxycarbonylamino)butanoic acid

HRID 2220105Notes

Reaction equation

HRID 2220105 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C:3]([CH3:6])([CH3:5])[CH3:4].C([O-])(O)=O.[Na+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C([O-])([O-])=O.[Na+].[Na+]>O>[CH2:19]([O:18][C:16]([NH:1][CH:2]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:7]([OH:9])=[O:8])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 164608L-tert-LeucineHCID 516892Sodium Bicarbonate

Product 1

HCID 34012063,3-dimethyl-2-(phenylmethoxycarbonylamino)butanoic acidYield 817.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of L-tert-leucine (1) (50.0 g, 38.0 mmol) and NaHCO3 (96.0 g, 114 mmol) in ice (500 g) and water (500 ml) was added benzyl chloroformate (65.0 ml, 74.0 mmol) and the reaction stirred at 0° C. for 3 hours then at room temperature for 18 hours. 0.1N Na2CO3 was added until the oily layer dissolved and the solution was washed with 10% EtOAc in hexanes (2×500 ml). The iced aqueous phase was acidified to pH 1 using 12N HCl then extracted using EtOAc (3×350 ml). The combined organic extracts were dried over Na2SO4, filtered and evaporated to give the title compound as a colorless oil (82.4 g, 81.5% yield): 1H-NMR (500 MHz, CDCl3) δ1.02 (s, 9H), 4.22 (d, 1H), 5.10–5.14 (m, 2H), 5.31 (d, 1H), 7.26–7.37 (m, 5H).

Workup

  1. waitat room temperature for 18 hours
  2. dissolutiondissolved
  3. washthe solution was washed with 10% EtOAc in hexanes (2×500 ml)
  4. extractionthen extracted
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6975cd4606154ad79666b1a5c8a0843d
Source dataset
uspto-grants-2008_08
Patent number
US07417029B2

Reaction notes

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