Sodium Chloride → [9-[(Cyclopentyl)methyl]-5-carbamoylcarbazol-4-yl]oxyacetic acid, methyl ester

HRID 51459Notes

Reaction equation

HRID 51459 reaction equation
[CH:1]1([CH2:6][N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:20])[C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][C:12]=3[C:21](=[O:23])[NH2:22])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33].[Na+].[Cl-]>CN(C=O)C.CCOC(C)=O.O>[CH:1]1([CH2:6][N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([O:20][CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][C:12]=3[C:21](=[O:23])[NH2:22])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 227382079-[(Cyclopentyl)methyl]-4-hydroxy-5-carbamoyl carbazole

Product 1

HCID 86756282[9-[(Cyclopentyl)methyl]-5-carbamoylcarbazol-4-yl]oxyacetic acid, methyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9-[(cyclopentyl)methyl]-4-hydroxy-5-carbamoyl carbazole (45 mg, 0.146 mmol) and Cs2CO3 (120 mg; 0.365 mmol) in 2 mL of DMF was treated with methyl bromoacetate (0.018 mL; 0.19 mmol). The reaction was stirred for 2 hours at ambient temperature, then it was diluted with EtOAc and H2O (10 mL each). The aqueous layer was saturated with solid NaCl extracted with EtOAc (2×10 mL). The combined organic layers were washed with H2O (2×25 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (elution with a gradient of 0% to 100% EtOAc/hexanes) followed by trituration with Et2O/EtOAc afforded 26 mg (0.0683 mmol; 47%) of title compound as a tan solid. MS (ES) m/e 381 (M+1), 364 (M+H—NH3), 439 (M+AcO−).

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe combined organic layers were washed with H2O (2×25 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude residue by flash chromatography on silica gel (
  7. washelution with a gradient of 0% to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6a5f189ad55b4ae3ac5d5a51c0b82905
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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