Methanol → HCID 67434996, compound

HRID 1946510Notes

Reaction equation

HRID 1946510 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[C:14]2[CH:15]([CH2:19][C:20]([O:22]CC)=[O:21])[CH2:16][CH2:17][CH2:18][C:13]=2[N:12]=[C:11]1[CH:25]([CH3:27])[CH3:26].CO.[OH-].[Na+]>CC1OCCC1>[NH3:10].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[C:14]2[CH:15]([CH2:19][C:20]([OH:22])=[O:21])[CH2:16][CH2:17][CH2:18][C:13]=2[N:12]=[C:11]1[CH:25]([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 58460196HCID 58460196, compound

Product 1

HCID 67434996HCID 67434996, compound

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent2×

Procedure

Intermediate 46 (35 mg) was dissolved in 2 ml of MeTHF. Potassium trimethylsilanoate (12.19 mg) was added and the mixture stirred at room temperature overnight. 2 ml further MeTHF was added to the reaction, followed by Methanol. 4 M equivalent of sodium hydroxide was added and the reaction stirred at 50° C. for 2 hours. The reaction mixture passed through an SCX ion exchange column (10 g) and eluted with 2M Ammonia and methanol. (28 mg). LC/MS MH+ 381, Rt 2.06 min (5 min run, TFA modifier).

Workup

  1. stirringthe reaction stirred at 50° C. for 2 hours
  2. washeluted with 2M Ammonia and methanol
  3. customLC/MS MH+ 381, Rt 2.06 min (5 min run, TFA modifier)

Sources & evidence

ORD record
ord-228637711c7344f99f8d4ac459675eee
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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