Water → 16874-08-1

HRID 2185582Notes

Reaction equation

HRID 2185582 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].O.[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(OC(C)(C)C)(=O)C>[CH3:2][C:3]([O:8][C:7](=[O:9])[C@H:2]([C@H:3]([CH2:5][CH3:6])[CH3:4])[NH2:1])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6306L-IsoleucineHCID 10340Sodium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 701053916874-08-1Yield 61%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

To an ice-bath cooled slurry of L-isoleucine (301.0 g; 2.29 mol) in tert-butyl acetate (2.5 L), 70% aq HClO4 (208 mL, 2.43 mol) was slowly added. The mixture was kept stirring for 10 days at room temperature. Then water (0.5 L) was poured into, followed by cooling in an ice bathand addition of NaOH pellets (100 g) and Na2CO3 (110 g) so that pH turned to basic. The mixture was extracted with EtOAc (4×0.5 L); the combined organic phases were washed with water (2×0.5 L) and brine (0.3 L), at last dried over Na2SO4. After careful removal of solvents in vacuo, the desired compound was obtained (262.2 g; 1.40 mol) and stored at −18° C. No further purification was required on the basis of TLC and NMR data. Yield 61%.

Workup

  1. additionwas slowly added
  2. extractionThe mixture was extracted with EtOAc (4×0.5 L)
  3. washthe combined organic phases were washed with water (2×0.5 L) and brine (0.3 L)
  4. dry with materialat last dried over Na2SO4
  5. customAfter careful removal of solvents in vacuo

Sources & evidence

ORD record
ord-f5400278baeb426b938495f3c6c50929
Source dataset
uspto-grants-2002_06
Patent number
US06403055B1

Reaction notes

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