2-Amino-3-hydroxybutanoic acid → HCID 19347672, compound

HRID 1395912Notes

Reaction equation

HRID 1395912 reaction equation
[NH2:1][CH:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[OH:4].[CH2:9](O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[NH2:1][CH:2]([CH:3]([OH:4])[CH3:5])[C:6]([O:8][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 2052-Amino-3-hydroxybutanoic acidHCID 6101p-Toluenesulfonic acidHCID 81931-Dodecanol

Product 1

HCID 19347672HCID 19347672, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of DL-threonine 26 (5 g, 41.9 mmol) in toluene (100 mL) was added 1-dodecanol 2 (7 g, 37.7 mmol) in one lot, followed by pTSA (8.77 g, 46.16 mmol). After addition, the temperature of the reaction mixture was slowly raised to reflux temperature and the water was separated azeotropically. 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 27 (11 g, yield: 91%) 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-e48007aa94b54ef9bfce288b3810e7a0
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

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