Chloroacetic Acid → HCID 10385803, compound

HRID 855553Notes

Reaction equation

HRID 855553 reaction equation
[CH:1]1([CH2:6][CH:7]([C:16]2[CH:17]=[N:18][C:19]([SH:22])=[CH:20][CH:21]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:26][C:27]([OH:29])=[O:28]>CN(C=O)C>[CH:1]1([CH2:6][CH:7]([C:16]2[CH:21]=[CH:20][C:19]([S:22][CH2:26][C:27]([OH:29])=[O:28])=[N:18][CH:17]=2)[C:8](=[O:9])[NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 300Chloroacetic Acid2×HCID 24758Sodium hydride2×HCID 178522583HCID 178522583, compound

Product 1

HCID 10385803HCID 10385803, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-Cyclopentyl-2-(6-mercaptopyridin-3-yl)-N-thiazol-2-ylpropionamide (EXAMPLE 66, 50 mg, 150 μmol) was added to a stirred suspension of NaH (12 mg of a 60% dispersion in mineral oil, 300 μmol) in anhydrous DMF (0.8 mL). After 5 min, a solution of chloroacetic acid (14 mg, 150 μmol) in anhydrous DMF (0.4 mL) was added. The reaction was stirred for 15 min, then more NaH (10 mg of a 60% dispersion in mineral oil, 250 μmol) and chloroacetic acid (14 mg, 150 μmol) were added. After 15 min, the reaction mixture was partitioned between EtOAc (10 mL) and saturated aqueous Na2CO3—H2O (1:1, 15 mL). The aqueous phase was acidified to pH 2.5 with 2M HCl, then the resulting precipitate was extracted into EtOAc (15 mL). The EtOAc solution was washed with brine (5 mL), dried (MgSO4), filtered, concentrated, and recrystallised (CH2Cl2—IH) to give the title compound: RTA=3.52 min; m/z (ES+)=392.2 [M+H]+.

Workup

  1. waitAfter 15 min
  2. customthe reaction mixture was partitioned between EtOAc (10 mL) and saturated aqueous Na2CO3—H2O (1:1, 15 mL)
  3. extractionthe resulting precipitate was extracted into EtOAc (15 mL)
  4. washThe EtOAc solution was washed with brine (5 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customrecrystallised (CH2Cl2—IH)

Sources & evidence

ORD record
ord-0a889bd2292545b9bfc3037956f82de8
Source dataset
uspto-grants-2007_08
Patent number
US07262196B2

Reaction notes

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