Methyl 2,6-difluoro-4-[(3-methoxymethoxy-5,5,8,8,-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate → 2,6-Difluoro-4-[(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoic acid

HRID 1935655Notes

Reaction equation

HRID 1935655 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([NH:12][C:13]([C:15]2[C:24]([O:25]COC)=[CH:23][C:22]3[C:21]([CH3:30])([CH3:29])[CH2:20][CH2:19][C:18]([CH3:32])([CH3:31])[C:17]=3[CH:16]=2)=[O:14])[CH:9]=[C:8]([F:33])[C:3]=1[C:4]([O:6]C)=[O:5]>CO.Cl>[F:1][C:2]1[CH:11]=[C:10]([NH:12][C:13]([C:15]2[C:24]([OH:25])=[CH:23][C:22]3[C:21]([CH3:29])([CH3:30])[CH2:20][CH2:19][C:18]([CH3:32])([CH3:31])[C:17]=3[CH:16]=2)=[O:14])[CH:9]=[C:8]([F:33])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 22465055Methyl 2,6-difluoro-4-[(3-methoxymethoxy-5,5,8,8,-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate2×

Product 1

HCID 98658752,6-Difluoro-4-[(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 2,6-difluoro-4-[(3-methoxymethoxy-5,5,8,8,-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate (Compound A, 113 mg, 0.26 mmol) in 6 ml of methanol and 3 drops of conc. HCl was stirred at room temperature for overnight and then concentrated to dryness. The solid was recrystallized from ethyl ether: hexane to give the title compound as a white solid.

Workup

  1. concentrationconcentrated to dryness
  2. customThe solid was recrystallized from ethyl ether

Sources & evidence

ORD record
ord-e2ad914de7c44c39ab4a62398ca80de4
Source dataset
uspto-grants-2002_05
Patent number
US06387950B2

Reaction notes

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