Acetonitrile → HCID 68688141, compound

HRID 2244694Notes

Reaction equation

HRID 2244694 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8](OS(C)(=O)=O)[C@@H:7]([NH:15][C:16]([C:18]2[S:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[O:17])[CH2:6]1)=[O:4].[C:24](#[N:26])C>[C-]#N.C([N+](CC)(CC)CC)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([C:24]#[N:26])[CH:7]([NH:15][C:16]([C:18]2[S:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[O:17])[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 58826456HCID 58826456, compound

Product 1

HCID 68688141HCID 68688141, compound

Reagents, catalysts & solvents 1

HCID 3014735Tetraethylammonium cyanideCatalyst

Procedure

A solution of (1R,3S,4R)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methanesulfonyloxy-cyclopentanecarboxylic acid methyl ester (150 mg) in acetonitrile (5 ml) was treated with tetraethylammonium cyanide (74 mg) and heated to reflux for 4 hrs. The reaction mixture was concentrated. The crude product was isolated by column chromatography (silica gel; gradient: CH2Cl2→CH2Cl2/MeOH 95:5) to give 3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-cyano-cyclopentanecarboxylic acid methyl ester (100 mg) as light brown oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hrs
  3. concentrationThe reaction mixture was concentrated
  4. customThe crude product was isolated by column chromatography (silica gel; gradient: CH2Cl2→CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-1d956942314b421cb5f0f0069f1d5bbc
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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