Hydrochloric Acid → HCID 58418192, compound

HRID 588508Notes

Reaction equation

HRID 588508 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C@@H:13]([C:15]1[CH:19]=[C:18]([C:20]([O:22]CC)=[O:21])[O:17][N:16]=1)[CH3:14])=[O:11].[OH-].[Li+].Cl>CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C@@H:13]([C:15]1[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[O:17][N:16]=1)[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58418129HCID 58418129, compound

Product 1

HCID 58418192HCID 58418192, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the crude (R)-ethyl 3-(1-(benzofuran-2-carboxamido)ethyl)isoxazole-5-carboxylate was added lithium hydroxide (0.572 mL, 1.0 M in water), and MeOH (1.0 mL). The mixture was shaken at rt for 16 h, then hydrochloric acid (0.214 mL, 4.0 M in 1,4-dioxane) was added to acidify the reaction. Most of the solvent was evaporated. To the residue was added water (1.0 mL) and DCE (3 mL). After separation, the aqueous layer was extracted with DCE (3 mL). The combined organic phases were concentrated to give crude (R)-3-(1-(benzofuran-2-carboxamido)ethyl)isoxazole-5-carboxylic acid.

Workup

  1. customthe reaction
  2. customMost of the solvent was evaporated
  3. additionTo the residue was added water (1.0 mL) and DCE (3 mL)
  4. customAfter separation
  5. extractionthe aqueous layer was extracted with DCE (3 mL)
  6. concentrationThe combined organic phases were concentrated

Sources & evidence

ORD record
ord-af73ce676e3542eeb5e519d9ae18011e
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

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