Cesium carbonate → HCID 86756279, compound

HRID 51433Notes

Reaction equation

HRID 51433 reaction equation
[CH2:1]([N:8]1[C:20]2[CH2:19][CH2:18][CH2:17][CH:16]([C:21](=[O:23])[NH2:22])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][C:13]=2[OH:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:32][C:33]([O:35][CH3:36])=[O:34]>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH2:19][CH2:18][CH2:17][CH:16]([C:21](=[O:23])[NH2:22])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][C:13]=2[O:24][CH2:32][C:33]([O:35][CH3:36])=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 227382229-Benzyl-4-carbamoyl-5-hydroxy-1,2,3,4-tetrahydrocarbazole

Product 1

HCID 86756279HCID 86756279, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 80 mg (0.25 mmol) of 9-benzyl-4-carbamoyl-5-hydroxy-1,2,3,4-tetrahydrocarbazole in 2.5 mL of DMF was treated with 61 mg (0.30 mmol) of Cs2CO3 followed by 26 mg (0.30 mmol) of methyl bromoacetate. The mixture was stirred at room temperature until tlc indicated complete consumption of starting material (2 hours). The reaction was diluted with H2O (10 mL) and was extracted with EtOAc (3×10 mL). The combined organic layers were washed with H2O (3×20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by radial chromatography (SiO2; 2.5% MeOH in CH2Cl2) to afford 50 mg (0.13 mmol; 51%) of [9-benzyl-4-carbamoyl-1,2,3,4-tetrahydrocarbazole-5-yl]oxyacetic acid, methyl ester as an oil. 1H NMR (CDCl3) δ7.33-7.21 (m, 3H), 7.05-6.98 (m, 3H), 6.98 (d, 1H, J=7.4 Hz), 6.46 (br s, 1H), 6.37 (d, 1H, J=7.7 Hz), 5.52 (br s, 1H), 5.23 (d, 1H, J=4.9 Hz) 4.79-4.70 (m, 2H), 4.20-4.15 (m, 1H), 3.81 (s, 3H), 2.79-2.69 (m, 1H), 2.63-2.49 (m, 1H), 2.43-2.35 (m, 1H), 2.25-2.09 (m, 1H), and 1.99-1.78 (m, 2H). IR (CHCl3, cm−1) 1759, 1670, 1497, 1453, 1440, and 1132. MS (ES) m/e 393 (M+1).

Workup

  1. customconsumption of starting material (2 hours)
  2. additionThe reaction was diluted with H2O (10 mL)
  3. extractionwas extracted with EtOAc (3×10 mL)
  4. washThe combined organic layers were washed with H2O (3×20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by radial chromatography (SiO2; 2.5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-aa58b67705f64403b719e3009c406993
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

Loading…