DL-alanine → HCID 86722541, compound

HRID 1395923Notes

Reaction equation

HRID 1395923 reaction equation
[NH2:1][CH:2]([C:4]([OH:6])=[O:5])[CH3:3].[CH3:7][CH:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[NH2:1][CH:2]([CH3:3])[C:4]([O:6][CH:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH3:7])[CH3:19])=[O:5]

Participants

5

Reactant 3

HCID 602DL-alanineHCID 6101p-Toluenesulfonic acidHCID 15449Tridecan-2-ol

Product 1

HCID 86722541HCID 86722541, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of DL-alanine 1 (15 g, 168.5 mmol) in toluene (300 mL) was added 2-tridecanol 68 (30.3 g, 151.68 mmol) in one lot, followed by pTSA (35.26 g, 185.38 mmol). After the 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 69 (36 g, yield: 78.9%) as a liquid.

Workup

  1. additionAfter the 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-8db0c7c159aa4b19bafc627072e84c44
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

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