Iodoethane → Ethyl 2,6-difluoro-4-[(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate

HRID 1935656Notes

Reaction equation

HRID 1935656 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([NH:11][C:12]([C:14]2[C:23]([OH:24])=[CH:22][C:21]3[C:20]([CH3:26])([CH3:25])[CH2:19][CH2:18][C:17]([CH3:28])([CH3:27])[C:16]=3[CH:15]=2)=[O:13])[CH:8]=[C:7]([F:29])[C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].I[CH2:37][CH3:38]>CC(C)=O>[F:1][C:2]1[CH:10]=[C:9]([NH:11][C:12]([C:14]2[C:23]([OH:24])=[CH:22][C:21]3[C:20]([CH3:25])([CH3:26])[CH2:19][CH2:18][C:17]([CH3:28])([CH3:27])[C:16]=3[CH:15]=2)=[O:13])[CH:8]=[C:7]([F:29])[C:3]=1[C:4]([O:6][CH2:37][CH3:38])=[O:5]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 98658752,6-Difluoro-4-[(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoic acid2×

Product 1

HCID 22465056Ethyl 2,6-difluoro-4-[(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2,6-difluoro-4-[(3-hydroxy-5,5,8,8,-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoic acid (Compound B, 56 mg, 0.13 mmol) in 4 ml of acetone was added potassium carbonate (36 mg, 0.26 mmol) and iodoethane (0.012 ml, 0.14 mmol). The reaction mixture was stirred at room temperature for 4 hours then concentrated and purified by column chromatography with ethyl acetate: hexane (1:9) to yield the title compound as a white solid.

Workup

  1. concentrationthen concentrated
  2. custompurified by column chromatography with ethyl acetate: hexane (1:9)

Sources & evidence

ORD record
ord-2e0a59723ce040b994feb10b7622bb61
Source dataset
uspto-grants-2002_05
Patent number
US06387950B2

Reaction notes

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