Hydrochloric Acid → HCID 765906, compound

HRID 1882946Notes

Reaction equation

HRID 1882946 reaction equation
[C:1]([C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([O:16]C)=[O:15])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Li+].Cl>CO>[C:1]([C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([OH:16])=[O:15])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 772645HCID 772645, compound

Product 1

HCID 765906HCID 765906, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirring solution of methyl 2-(4-tert-butylbenzoyl-amino)benzoate (10.4 g, 33.4 mmol) and THF (200 mL) was treated with 1 M aqueous lithium hydroxide (40 mL) and methanol (80 mL). After stirring over night at room temperature, the mixture was treated with 1 M aqueous HCl (40 mL) and the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (400 mL) and brine (100 mL). The organic phase was separated, then dried with MgSO4, filtered and concentrated in vacuo to give 9.69 g (98%) of a white powder.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between ethyl acetate (400 mL) and brine (100 mL)
  3. customThe organic phase was separated
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2602ed5e26304d29a755808754d1353c
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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