Water → HCID 68508315, compound

HRID 1256873Notes

Reaction equation

HRID 1256873 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][N:6]([C:9](=[O:34])[CH:10]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:11]([NH:13][S:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1)(=[O:16])=[O:15])=[O:12])[CH2:7][CH3:8])C.O.[OH-].[Na+]>C1COCC1>[CH2:27]([CH:10]([C:11]([NH:13][S:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1)(=[O:16])=[O:15])=[O:12])[C:9]([N:6]([CH2:7][CH3:8])[CH2:5][C:4]([OH:35])=[O:3])=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68510487HCID 68510487, compound

Product 1

HCID 68508315HCID 68508315, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of the compound (250 mg) obtained by Example 2 in THF (10 mL)/water (3 mL) was added 1 mol/L aqueous sodium hydroxide solution (1.5 mL) at room temperature, and the mixture was stirred for 2.5 hr. After concentration under reduced pressure, the residue was adjusted to pH=1-2 by the addition of 1 mol/L hydrochloric acid and extracted with ethyl acetate (50 mL×2). The organic layer was washed with saturated brine and concentrated under reduced pressure to give the title compound (211 mg) as a white solid.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. additionthe residue was adjusted to pH=1-2 by the addition of 1 mol/L hydrochloric acid
  3. extractionextracted with ethyl acetate (50 mL×2)
  4. washThe organic layer was washed with saturated brine
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ed5d73815714820bb434a25b566ece3
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

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