Hydrochloric Acid → HCID 52914395, compound

HRID 2177675Notes

Reaction equation

HRID 2177675 reaction equation
[ClH:1].[C:2]1([S:8]([CH2:11][C:12]2[C:17]([C:18]([OH:20])=[O:19])=[C:16]([O:21][CH2:22][CH2:23][NH:24]C(OC(C)(C)C)=O)[C:15]([C:32]3[CH:36]=[CH:35][O:34][CH:33]=3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1>[ClH:1].[NH2:24][CH2:23][CH2:22][O:21][C:16]1[C:15]([C:32]2[CH:36]=[CH:35][O:34][CH:33]=2)=[CH:14][CH:13]=[C:12]([CH2:11][S:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:10])=[O:9])[C:17]=1[C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 671076826-(Benzenesulphonylmethyl)-2-[2-(t-butoxycarbonyl)aminoethoxy]-3-(furan-3-yl)benzoic acid2×

Product 1

HCID 52914395HCID 52914395, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride (4M in dioxane, 2 ml) was added to a solution of 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonyl)aminoethoxy]-3-(furan-3-yl)benzoic acid (Intermediate 6, 0.018 g) in dioxane (0.5 ml) and the resultant mixture was stirred at room temperature for 2 hours. The mixture was evaporated to dryness and the residue was triturated with ether. The solid was collected by filtration then purified by chromatography on silica, eluting with a mixture of DCM, methanol, acetic acid and water in a ratio of 240:20:3:2 changing to 120:15:3:2. After evaporation of the solvent, the residue was treated with hydrochloric acid (1M) and evaporated to dryness to give 2-(2-aminoethoxy)-6-(benzenesulphonylmethyl)-3-(furan-3-yl)benzoic acid hydrochloride (0.008 g) as a white solid.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue was triturated with ether
  3. filtrationThe solid was collected by filtration
  4. customthen purified by chromatography on silica
  5. washeluting with a mixture of DCM, methanol, acetic acid and water in a ratio of 240:20:3:2 changing to 120:15:3:2
  6. customAfter evaporation of the solvent
  7. additionthe residue was treated with hydrochloric acid (1M)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-2c6b655937a04475acc0b399673385bd
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

Loading…