Water → N-(3-Acetylthio-2-methylpropanoyl)-N-cyclopentylglycine

HRID 543261Notes

Reaction equation

HRID 543261 reaction equation
C([O:5][C:6](=[O:23])[CH2:7][N:8]([C:14](=[O:22])[CH:15]([CH3:21])[CH2:16][S:17][C:18](=[O:20])[CH3:19])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C.C[Si](Cl)(C)C.[I-].[Na+].O>C(#N)C>[C:18]([S:17][CH2:16][CH:15]([CH3:21])[C:14]([N:8]([CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)[CH2:7][C:6]([OH:23])=[O:5])=[O:22])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 13599173HCID 13599173, compound

Product 1

HCID 13599174N-(3-Acetylthio-2-methylpropanoyl)-N-cyclopentylglycine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 80.1 g (0.23 mol) of N-(3-acetylthio-2-methyl-propanoyl)-N-cyclopentyl glycine t-butyl ester, 37.9 g (0.35 mol) of trimethysilyl chloride, and 52.5 g (0.35 mol) of sodium iodide in 300 ml of acetonitrile was heated between 45°-50° C. for 30 minutes. Following the addition of 50 ml of water, the mixture was concentrated in vacuo. The residue was rendered basic with 400 ml of saturated aqueous NaHCO3, washed three times with ethyl acetate, acidified with concentrated HCl, and extracted three times with ethyl acetate. These later organic extracts were combined, dried over MgSO4, filtered, and concentrated in vacuo to afford 60 g (91%) of the crude product. Purification via high pressure liquid chromatography (HPLC) [ethyl acetate/hexane/acetic acid (60/40/2)] afforded N-(3-acetylthio-2-methylpropanoyl)-N-cyclopentyl glycine as an oil.

Workup

  1. temperaturewas heated between 45°-50° C. for 30 minutes
  2. concentrationthe mixture was concentrated in vacuo
  3. washwashed three times with ethyl acetate
  4. extractionextracted three times with ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford 60 g (91%) of the crude product
  9. customPurification via high pressure liquid chromatography (HPLC) [ethyl acetate/hexane/acetic acid (60/40/2)]

Sources & evidence

ORD record
ord-ae031a1723a04b1da1c4b696c9cf40b0
Source dataset
uspto-grants-1987_04
Patent number
US04661515

Reaction notes

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