Water → HCID 22272880, compound

HRID 1064362Notes

Reaction equation

HRID 1064362 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:18]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:17][C:7]2[N:8]=[C:9]([S:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[NH:10][C:6]=2[CH:5]=1.[OH2:25].[O:26]1[CH2:30]C[CH2:28][CH2:27]1>C(N(CC)CC)C.BrCC(OC)=O>[Cl:3][C:4]1[C:18]([N:19]2[CH2:20][CH2:21][N:22]([CH2:28][C:27]([O:26][CH3:30])=[O:25])[CH2:23][CH2:24]2)=[CH:17][C:7]2[N:8]=[C:9]([S:11][CH:12]([CH2:13][CH3:14])[CH2:15][CH3:16])[NH:10][C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 69800449HCID 69800449, compound

Product 1

HCID 22272880HCID 22272880, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 60984Methyl bromoacetateSolvent

Procedure

To a solution of 82 mg of the compound of Example 1 in 2 ml of tetrahydrofuran, 0.14 ml of triethylamine and 0.017 ml of methyl bromoacetate were added by the order stated, and stirred for 3 hours at room temperature. Water was added to the solution which then was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried on anhydrous sodium sulfate. After distilling the solvent off under reduced pressure, the residue was separated and purified on silica gel column chromatography (chloroform/methanol=20/1) to provide 80 mg of the title compound.

Workup

  1. extractionthen was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. distillationAfter distilling the solvent off under reduced pressure
  5. customthe residue was separated
  6. custompurified on silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-c3cb643a3fd843e2a4248651b6f19b74
Source dataset
uspto-grants-2005_11
Patent number
US06969712B2

Reaction notes

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