HCID 11504863, compound → HCID 11611914, compound

HRID 908517Notes

Reaction equation

HRID 908517 reaction equation
C([N:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]1=[O:41])(=O)C1C=CC=CC=1.CO[Na]>CO>[C:22]([NH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:11]1[CH:12]=[CH:13][C:14](=[O:15])[NH:9][C:10]1=[O:41])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 11504863HCID 11504863, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 11611914HCID 11611914, compoundYield 156%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 18 (187 mg; 0.35 mmol) was dissolved and stirred in a solution of MeONa 0.2 M in MeOH (17 ml) at room temperature. After 24 hours the pH was adjusted to 7 with Dowex 50WX 8-200 ion exchange resin. The resin was removed by filtration and washed with MeOH. The solution was evaporated and the residue was purified by flash chromatography with DCM/MeOH 90:10 as eluent which gave the title compound as a white foam (240 mg, 52%). Rf: 0.50 in DCM/MeOH 90:10.

Workup

  1. customThe resin was removed by filtration
  2. washwashed with MeOH
  3. customThe solution was evaporated
  4. customthe residue was purified by flash chromatography with DCM/MeOH 90:10 as eluent which

Sources & evidence

ORD record
ord-6d8f0216c6524bb9a2987f2c7eb89328
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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