Methanol → HCID 67110362, compound

HRID 2080674Notes

Reaction equation

HRID 2080674 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CO.FC(F)(F)C(O)=O.[CH2:16]([S:18]([C:21]1[CH:51]=[CH:50][C:24]([O:25][C:26]2[C:40]([CH2:41]NC(=O)/C=C\C(O)=O)=[CH:39][C:29]3[NH:30][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[N:32][C:28]=3[CH:27]=2)=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:17]>C(Cl)(Cl)Cl.[Cl-].[NH4+]>[CH2:16]([S:18]([C:21]1[CH:51]=[CH:50][C:24]([O:25][C:26]2[C:40]([CH2:41][CH2:1][OH:4])=[CH:39][C:29]3[NH:30][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[N:32][C:28]=3[CH:27]=2)=[CH:23][CH:22]=1)(=[O:19])=[O:20])[CH3:17]

Participants

6

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 67110335HCID 67110335, compound

Product 1

HCID 67110362HCID 67110362, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 25517Ammonium ChlorideSolvent

Procedure

9.0 mg of the obtained alcohol compound was dissolved in 1 ml of trifluoroacetic acid, and stirred at room temperature for 1.5 hours. The solvent was evaporated away, and the residue was diluted with chloroform and neutralized with aqueous saturated sodium hydrogencarbonate solution. This was extracted with chloroform, and the organic layer was washed with saturated saline water. After dried, the solvent was evaporated away under reduced pressure, to obtain 9.0 mg of a trifluoroacetate. Potassium carbonate was added to a methanol (1 ml) solution of 9.0 mg of the trifluoroacetate, and stirred at room temperature for 30 minutes. This was diluted with chloroform, and aqueous saturated ammonium chloride solution was added to it, extracted with chloroform, and the organic layer was washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water. After dried, the solvent was evaporated away under reduced pressure, and the residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain 6.6 mg of the entitled compound as a colorless amorphous substance.

Workup

  1. additionwas added to it
  2. extractionextracted with chloroform
  3. washthe organic layer was washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water
  4. customAfter dried
  5. customthe solvent was evaporated away under reduced pressure
  6. customthe residue was purified
  7. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-0f10ca19e2524021899978e8918c1b85
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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