Water → HCID 10272714, compound

HRID 2215188Notes

Reaction equation

HRID 2215188 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([OH:17])[CH:13]=[CH:14][CH:15]=2)[C:10]2[CH:18]([C:23]([NH2:25])=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:33][C:34]([O:36][CH3:37])=[O:35].O>CN(C=O)C.CCOC(C)=O>[CH3:37][O:36][C:34](=[O:35])[CH2:33][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[C:10]1[CH:18]([C:23](=[O:24])[NH2:25])[CH2:19][CH2:20][CH2:21][CH2:22][C:9]=1[N:8]2[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 21055258HCID 21055258, compound

Product 1

HCID 10272714HCID 10272714, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 5-benzyl-1-hydroxy-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole-10-carboxylic acid amide (Part F; 275 mg; 0.822 mmol) and Cs2CO3 (670 mg; 2.06 mmol) in 8 mL of DMF was treated with methyl bromoacetate (0.100 mL; 1.07 mmol). After stirring overnight at ambient temperature, the reaction mixture was poured into water and EtOAc (20 mL each). The layers were separated, and the organic phase was washed with water (3×20 mL), dried over Na2SO4 and concentrated in vacuo. Purification by radial chromatography (CHCl3) afforded 205 mg (0.504 mmol; 61%) of the title ester as a white foam. ES-MS: 407 (M+1)+.

Workup

  1. customThe layers were separated
  2. washthe organic phase was washed with water (3×20 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by radial chromatography (CHCl3)

Sources & evidence

ORD record
ord-26a3baaaba1e48cb9b57947b27deac62
Source dataset
uspto-grants-2006_09
Patent number
US07109231B2

Reaction notes

Loading…