Hydrochloric Acid → [4-Acetylamino-3-(biphenyl-4-ylsulfanyl)-2-methyl-indol-1-yl]-acetic Acid

HRID 18497Notes

Reaction equation

HRID 18497 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([NH:15][C:16](=[O:18])[CH3:17])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:19])C.[C:21]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][C:24]([SH:27])=[CH:23][CH:22]=1.II.[OH-].[Na+].Cl>CN(C=O)C.O>[C:16]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[C:8]([S:27][C:24]1[CH:23]=[CH:22][C:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:26][CH:25]=1)=[C:7]([CH3:19])[N:6]2[CH2:5][C:4]([OH:3])=[O:20])(=[O:18])[CH3:17]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 14798Sodium HydroxideHCID 27604144-Phenylbenzene-1-thiolHCID 59431286Ethyl 2-(4-acetamido-2-methyl-1H-indol-1-yl)acetate

Product 1

HCID 24850440[4-Acetylamino-3-(biphenyl-4-ylsulfanyl)-2-methyl-indol-1-yl]-acetic AcidYield 37.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-acetylamino-2-methyl-indol-1-yl)-acetic acid ethyl ester (0.27 g) and biphenyl-4-thiol (0.19 g) in DMF (5 ml) was added iodine (0.25 g). After stirring at RT overnight 1M NaOH (3 ml) was added and the reaction stirred at RT for a further 12 hours. The reaction was poured into water, the pH adjusted to 3 using 1M HCl and the organics extracted with EtOAc. The EtOAc extractions were combined, washed with brine, dried (MgSO4) and evaporated under reduced pressure to give crude material. Purification using RPHPLC gave the title compound as a pink solid (0.16 g).

Workup

  1. additionwas added
  2. extractionthe organics extracted with EtOAc
  3. extractionThe EtOAc extractions
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto give crude material
  8. customPurification

Sources & evidence

ORD record
ord-01bbb7a7e0ec4ddea8d8826b83d044c8
Source dataset
uspto-grants-2010_06
Patent number
US07741360B2

Reaction notes

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