1,2-Dichloroethane → HCID 58218982, compound

HRID 1844654Notes

Reaction equation

HRID 1844654 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:13]1[C@@H:17]([CH2:18][CH2:19][CH2:20][CH2:21][C:22](O)=[O:23])[S:16][S:15][CH2:14]1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[S:15]1[CH2:14][CH2:13][C@H:17]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=2)[C:7]([O:9][CH3:10])=[O:8])=[O:23])[S:16]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 6112Lipoic acidHCID 135127Methyl 5-amino-2-hydroxybenzoate

Product 1

HCID 58218982HCID 58218982, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 5-amino-2-hydroxybenzoate (500 mg, 2.99 mmol) was taken up in DMF (15 mL) along with (R)-α-lipoic acid (TCI, 618 mg, 2.99 mmol) and EDC (630 mg, 3.3 mmol). The resulting reaction mixture was stirred at room temperature for 18 h and then diluted with EtOAc (60 mL). The organic layer was washed with water (3×10 mL), brine, dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (95% CH2Cl2, 5% MeOH) afforded 650 mg of (S)-methyl 5-(5-(1,2-dithiolan-3-yl)pentanamido)-2-hydroxybenzoate (61%). Mass calculated for C16H21NO4S2=355.09. found: [M+H]+=356.

Workup

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with water (3×10 mL), brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography (95% CH2Cl2, 5% MeOH)

Sources & evidence

ORD record
ord-bd4c6a675b8b44ba90c013a6b1324d78
Source dataset
uspto-grants-2015_02
Patent number
US08946451B2

Reaction notes

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