Methanol → HCID 57860410, compound

HRID 1513593Notes

Reaction equation

HRID 1513593 reaction equation
C([O:4][CH2:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([C:13]([C:15]1[S:27][C:26]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]([CH2:28][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:18](=[O:37])[C:17]=2[C:16]=1[O:38][CH3:39])=[O:14])[CH3:12])=[O:7])(=O)C.[OH-].[Na+].CO>C1COCC1.C(=O)([O-])O.[Na+]>[OH:4][CH2:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH3:12])[C:13]([C:15]1[S:27][C:26]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]([CH2:28][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:18](=[O:37])[C:17]=2[C:16]=1[O:38][CH3:39])=[O:14])=[O:7]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57860555HCID 57860555, compound

Product 1

HCID 57860410HCID 57860410, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixed solution of the compound of Example 504 (120 mg, 0.22 mmol) and 4N aqueous sodium hydroxide solution (2 mL) in THF (4 mL)-methanol (4 mL) was stirred at room temperature for 2 hr, the reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. Recrystallization of the crude solid from ethyl acetate-hexane gave the title compound (65 mg, 58%) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customRecrystallization of the crude solid from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5969d3f4612f476ca06d86ed55cce5fe
Source dataset
uspto-grants-2012_07
Patent number
US08217176B2

Reaction notes

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