Water → HCID 69620807, compound

HRID 1628261Notes

Reaction equation

HRID 1628261 reaction equation
C1C2C(COC([C@@H:18]([CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:19]([NH:21][C:22]3[N:26]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:25]=[C:24]([C:33]4[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=4)[CH:23]=3)=[O:20])=O)C3C(=CC=CC=3)C=2C=CC=1.CCCC[N+:50](CCCC)(CCCC)CCCC.[F-].O>C(Cl)Cl>[NH2:50][C@@H:18]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:19]([NH:21][C:22]1[N:26]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:25]=[C:24]([C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)[CH:23]=1)=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86664831HCID 86664831, compound

Product 1

HCID 69620807HCID 69620807, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a rt solution of 26.B (341 mg, 0.63 mmol) in CH2Cl2 (5 mL) was added TBAF (available from Aldrich) (1.0 M, 3.2 mL, 3.2 mmol). The resulting mixture was stirred at rt for 12 hr, treated with water (15), and extracted with 30% iPrOH/CHCl3 (3×15 mL). The combined organic layers were washed with water, brine and dried over MgSO4. After removal of organic solvent under reduced pressure, purification of the residue by flash chromatography on silica gel using 0-10% MeOH/CH2Cl2 for elution gave the title product 26.C as colorless solid (141 mg, 71%).

Workup

  1. extractionextracted with 30% iPrOH/CHCl3 (3×15 mL)
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over MgSO4
  4. customAfter removal of organic solvent
  5. customunder reduced pressure, purification of the residue by flash chromatography on silica gel using 0-10% MeOH/CH2Cl2
  6. washfor elution

Sources & evidence

ORD record
ord-6e0ddedc2aed40aabd842ba6d8756655
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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