Sodium Hydroxide → HCID 51348299, compound

HRID 1844655Notes

Reaction equation

HRID 1844655 reaction equation
[S:1]1[CH2:5][CH2:4][C@H:3]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=2)[C:18]([O:20]C)=[O:19])=[O:11])[S:2]1.[OH-].[Na+]>C1COCC1.O>[S:1]1[CH2:5][CH2:4][C@H:3]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=2)[C:18]([OH:20])=[O:19])=[O:11])[S:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58218982HCID 58218982, compound

Product 1

HCID 51348299HCID 51348299, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-methyl 5-(5-(1,2-dithiolan-3-yl)pentanamido)-2-hydroxybenzoate (650 mg, 1.83 mmol) was taken up in 6 mL of THF and NaOH (220 mg, 5.5 mmol) was added as a solution in 6 mL of H2O. The resulting reaction mixture was stirred at room temperature for 8 h and then concentrated under reduced pressure. Enough 1 N HCl was added to the aqueous layer to adjust the pH to 2 and the resulting mixture was extracted with EtOAc (3×20 mL). The combined organic layers were washed with water (2×20 mL), brine, dried (Na2SO4) and concentrated under reduced pressure to afford (S)-5-(5-(1,2-dithiolan-3-yl)pentanamido)-2-hydroxybenzoic acid. Mass calculated for C15H19NO4S2: 341.08. found: [M+H]+=342.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated under reduced pressure
  3. additionEnough 1 N HCl was added to the aqueous layer
  4. extractionthe resulting mixture was extracted with EtOAc (3×20 mL)
  5. washThe combined organic layers were washed with water (2×20 mL), brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8b3789823804d958163a9572162ac1a
Source dataset
uspto-grants-2015_02
Patent number
US08946451B2

Reaction notes

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