Sulfuric Acid → Caproyl proline

HRID 1502597Notes

Reaction equation

HRID 1502597 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[C:9](Cl)(=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH-].[Na+].S(=O)(=O)(O)O>O>[C:9]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])(=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 66982Decanoyl chlorideHCID 145742L-Proline

Product 1

HCID 18632633Caproyl prolineYield 92.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Proline (manufactured by Ajinomoto Co., Inc., 34.54 g) was dissolved in water (100 g), and decanoyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd., 52.01 g) and 25% aqueous sodium hydroxide solution were added while adjusting to pH 12. The mixture was neutralized with 75% sulfuric acid, and the aqueous layer was removed. Water and ethyl acetate were further added, and the aqueous layer was removed. Ethyl acetate was evaporated under reduced pressure to give decanoyl proline (68.12 g).

Workup

  1. customthe aqueous layer was removed
  2. additionWater and ethyl acetate were further added
  3. customthe aqueous layer was removed
  4. customEthyl acetate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c675f5da2bb54573ab36f57188f775b5
Source dataset
uspto-grants-2015_12
Patent number
US09211245B2

Reaction notes

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