1,2-Dichloroethane → alpha.-Lipoamide

HRID 925474Notes

Reaction equation

HRID 925474 reaction equation
[CH2:1]1[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[S:4][S:3][CH2:2]1.O[N:14]1C(=O)CCC1=O.C(Cl)CCl>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]1[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH2:14])=[O:12])[S:4][S:3][CH2:2]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 6112Lipoic acidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 6992093alpha.-Lipoamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of lipoic acid (25.6 g, 124 mmol), N-hydroxysuccinimide (15.6 g, 136 mmol), and EDC (26.1 g, 136 mmol) in anhydrous CH2Cl2 (300 mL) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate (500 mL) and washed with H2O (500 mL), saturated aqueous NaHCO3 (500 mL), saturated aqueous NaCl (500 mL) and dried (MgSO4). The drying agent was removed by filtration and the filtrate was concentrated to dryness giving the product as a yellow sold (35.4 g, 94%).

Workup

  1. washwashed with H2O (500 mL), saturated aqueous NaHCO3 (500 mL), saturated aqueous NaCl (500 mL)
  2. dry with materialdried (MgSO4)
  3. customThe drying agent was removed by filtration
  4. concentrationthe filtrate was concentrated to dryness
  5. customgiving the product as

Sources & evidence

ORD record
ord-3646ace3abfa4db392ca85946365a1e6
Source dataset
uspto-grants-2016_03
Patent number
US09284305B2

Reaction notes

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