Methanol → HCID 67498223, compound

HRID 1628318Notes

Reaction equation

HRID 1628318 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:17]=[C:18]([N+:20]([O-])=O)[CH:19]=2)[O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:5]=[CH:4][N:3]=1.[NH4+].[OH-].CO>CCOC(C)=O>[NH2:20][C:18]1[CH:17]=[C:10]([CH:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=2)[CH:19]=1)[O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 67496336HCID 67496336, compound

Product 1

HCID 67498223HCID 67498223, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a rt solution of 65.D (476 mg, 1.58 mmol) in EtOAc (9 mL) was added SnCl2-2H2O (1.88 g, 7.93 mmol). The reaction solution was refluxed for 2.0 hr, cooled to rt, and treated with concentrated NH4OH (2.5 mL). To the resulting mixture was added MeOH (10 mL) followed by celite. Solid was filtered off and washed with MeOH, the liquid layers was collected and concentrated. Purification of the residue by flash chromatography on silica gel using 0-20% MeOH/CH2Cl2 for elution gave title product 65.E as colorless syrup (282 mg, 65%).

Workup

  1. temperatureThe reaction solution was refluxed for 2.0 hr
  2. filtrationSolid was filtered off
  3. washwashed with MeOH
  4. customthe liquid layers was collected
  5. concentrationconcentrated
  6. customPurification of the residue by flash chromatography on silica gel using 0-20% MeOH/CH2Cl2
  7. washfor elution

Sources & evidence

ORD record
ord-0fe26f0263a049e3bc5c8cd416d82925
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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