DL-leucine → HCID 5125084, compound

HRID 1395915Notes

Reaction equation

HRID 1395915 reaction equation
[NH2:1][CH:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[NH2:1][CH:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([O:9][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 857DL-leucineHCID 6101p-Toluenesulfonic acidHCID 81931-Dodecanol

Product 1

HCID 5125084HCID 5125084, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of DL-leucine 42 (20 g, 152 mmol) in toluene (400 mL) was added 1-dodecanol 2 (25.56 g, 137.2 mmol) in one lot, followed by pTSA (31.9 g, 167.7 mmol). After addition, the temperature of the reaction mixture was slowly raised to reflux temperature, the water was separated azeotropically, and the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum, the obtained residue was taken in ethyl acetate (200 mL) and washed with aqueous 5% Na2CO3 (3×50 mL) followed by brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 43 (42 g, yield: 91.9%) as a liquid.

Workup

  1. additionAfter addition
  2. temperaturethe temperature of the reaction mixture was slowly raised
  3. temperatureto reflux temperature
  4. customthe water was separated azeotropically
  5. concentrationThe reaction mixture was concentrated under vacuum
  6. washwashed with aqueous 5% Na2CO3 (3×50 mL)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0fd72ae3961e481da85ef8949825dc29
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

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