Sodium Iodide → N-(2-Acetylthio-3-methoxybenzoyl)-N-cyclopentylglycine

HRID 325499Notes

Reaction equation

HRID 325499 reaction equation
[C:1]([S:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)(=[O:3])[CH3:2].C([O:20][C:21](=[O:29])[CH2:22][NH:23][CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)(C)(C)C.[I-].[Na+].Cl[Si](C)(C)C>C(Cl)Cl.C(#N)C>[C:1]([S:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([N:23]([CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)[CH2:22][C:21]([OH:29])=[O:20])=[O:9])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 13298943Tert-butyl 2-(cyclopentylamino)acetateHCID 204652112-Acetylthio-3-methoxybenzoic acid

Product 1

HCID 20465214N-(2-Acetylthio-3-methoxybenzoyl)-N-cyclopentylglycine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

N,N1 -Dicyclohexylcarbodiimide (10.3 g, 50 mmol) in methylene chloride (80 ml) was added to 2-acetylthio-3-methoxybenzoic acid (11.3 g, 50 mmol) and N-cyclopentylglycine t-butyl ester (10.0 g, 50 mmol) in methylene chloride (300 ml) at 0°-5° C. Overnight stirring was followed by filtration and washing of the filtrate with dilute hydrochloric acid, sodium bicarbonate solution and brine. Drying and concentration gave a gum which was dissolved in acetonitrile (65 ml), combined with sodium iodide (11.2 g, 75 mmol) and heated to 40°-50° C. Chlorotrimethylsilane (8.1 g, 75 mmol) was introduced and the mixture was heated for 30 minutes, then quenched with water. The organic phase was washed with water, aqueous sodium thiosulfate and brine then concentrated. Aqueous sodium bicarbonate was added to the residue and the resulting solution was washed with methylene chloride and ether, then acidified and extracted with ethyl acetate. The organic portion was dried and concentrated and the residue passed through a silica gel column to provide the amorphous product.

Workup

  1. filtrationwas followed by filtration
  2. washwashing of the filtrate with dilute hydrochloric acid, sodium bicarbonate solution and brine
  3. customDrying
  4. concentrationconcentration
  5. customgave a gum which
  6. temperatureheated to 40°-50° C
  7. temperaturethe mixture was heated for 30 minutes
  8. customquenched with water
  9. washThe organic phase was washed with water, aqueous sodium thiosulfate and brine
  10. concentrationthen concentrated
  11. additionAqueous sodium bicarbonate was added to the residue
  12. washthe resulting solution was washed with methylene chloride and ether
  13. extractionextracted with ethyl acetate
  14. customThe organic portion was dried
  15. concentrationconcentrated
  16. customto provide the amorphous product

Sources & evidence

ORD record
ord-9046fd3a8a9440e1a2ddeace184d8694
Source dataset
uspto-grants-1984_04
Patent number
US04440941

Reaction notes

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