1,2-Dichloroethane → HCID 47456092, compound

HRID 1844648Notes

Reaction equation

HRID 1844648 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[NH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C(Cl)CCl>C(Cl)Cl>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([NH:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:10]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 338Salicylic AcidHCID 187201N-BOC-ethylenediamine

Product 1

HCID 47456092HCID 47456092, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Salicylic acid (4.3 g, 0.0312 mol) was taken up in 60 mL of CH2Cl2 along with tert-butyl 2-aminoethylcarbamate (5.0 g, 0.0312 mol) and EDC (6.6 g, 0.0343 mol). The resulting reaction mixture was stirred at room temperature for 8 h and then quenched with saturated aqueous NaHCO3. The organic layer was separated and washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (1:1 pentane/EtOAc) afforded 5.7 g of tert-butyl 2-(2-hydroxybenzamido)ethylcarbamate (65%). tert-Butyl 2-(2-hydroxybenzamido)ethylcarbamate (650 mg, 2.31 mmol) was taken up in 4 mL of 4 N HCl in dioxane and allowed to stir at room temperature for 2 h. The reaction mixture was diluted with EtOAc and concentrated under reduced pressure to afford the HCl salt of N-(2-aminoethyl)-2-hydroxybenzamide. This material was taken up in DMF (15 mL) along with (R)-α-lipoic acid (TCI, 478 mg, 2.31 mmol) along with EDC (443 mg, 2.54 mmol) and DIEA (1.2 mL, 6.93 mmol). The resulting reaction mixture was stirred at room temperature for 4 h and then diluted with EtOAc (60 mL). The organic layer was washed with water (4×5 mL), brine, dried (Na2SO4) and concentrated under reduced pressure to afford (S)—N-(2-(5-(1,2-dithiolan-3-yl)pentanamido)ethyl)-2-hydroxybenzamide (420 mg, 49%). Mass calculated for C17H24N2O3S2: 368.12. found: [M+H]+=369.

Workup

  1. customThe resulting reaction mixture
  2. customquenched with saturated aqueous NaHCO3
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by chromatography (1:1 pentane/EtOAc)

Sources & evidence

ORD record
ord-b9f820eca4c443909c83aff7817ae109
Source dataset
uspto-grants-2015_02
Patent number
US08946451B2

Reaction notes

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