Hydrochloric Acid → HCID 9900104, compound

HRID 1612420Notes

Reaction equation

HRID 1612420 reaction equation
C([S:4][CH2:5][CH2:6][CH2:7][CH:8]([C:20]([O:22]C)=[O:21])[O:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15]C)=[O:14])(=O)C.[OH-].[Na+].Cl>C1COCC1>[C:20]([CH:8]([O:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([OH:15])=[O:14])[CH2:7][CH2:6][CH2:5][SH:4])([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11573667HCID 11573667, compound

Product 1

HCID 9900104HCID 9900104, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-(4-acetylthio-1-methoxy-carbonylbutoxy)benzoate XV (8.00 g, 23.5 mmol) in THF (60 mL) was deoxygenated by bubbling N2 through the solution for 1 hour. To the solution was added deoxygenated 3 N NaOH (47 mL, 141 mmol) and the mixture was stirred for 24 hours at room temperature under N2. The mixture was acidified with 1 N HCl and extracted with EtOAc (3×300 mL). The organic extracts were washed with water (300 mL) and brine (300 mL), dried over MgSO4, filtered, and concentrated. The residual oil was dissolved in ether and the solution was concentrated to afford 3-(1-carboxy-4-mercaptobutoxy)-benzoic acid 14 (4.40 g, 16.3 mmol, 69%) as a white solid: 1H NMR (CDCl3) δ 1.40 (t, J=7.9 Hz, 1H), 1.83–1.99 (m, 2H), 2.11–2.22 (m, 2H), 2.63 (m, 2H), 4.76 (dd, J=7.3, 5.0 Hz, 1H), 7.23 (m, 1H), 7.38 (t, J=7.8 Hz, 1H), 7.49 (m, 1H), 7.72 (d, J=7.7 Hz, 1H); 13C NMR (CDCl3) δ 24.1, 29.6, 31.2, 75.5, 114.8, 122.1, 123.9, 129.9, 130.5, 157.6, 171.8, 177.1. Anal. Calcd for C12H14O5S: C, 53.32; H, 5.22; S, 11.86. Found: C, 53.04; H, 5.38; S, 11.58.

Workup

  1. customby bubbling N2 through the solution for 1 hour
  2. additionTo the solution was added
  3. extractionextracted with EtOAc (3×300 mL)
  4. washThe organic extracts were washed with water (300 mL) and brine (300 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe residual oil was dissolved in ether
  9. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-e0118810aae24537affd3bd29953fe99
Source dataset
uspto-grants-2006_01
Patent number
US06992215B2

Reaction notes

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