Sodium Hydroxide → HCID 9944251, compound

HRID 1612414Notes

Reaction equation

HRID 1612414 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]([C:16]([O:18]C)=[O:17])=[CH:12][C:3]=1[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][S:7][C:6]1=[O:11].[OH-:20].[Na+]>C1COCC1>[C:16]([C:13]1[CH:14]=[CH:15][C:2]([Cl:1])=[C:3]([CH2:4][CH:5]([CH2:10][CH2:9][CH2:8][SH:7])[C:6]([OH:11])=[O:20])[CH:12]=1)([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12144657HCID 12144657, compound

Product 1

HCID 9944251HCID 9944251, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(2-Chloro-5-methoxycarbonylbenzyl)-tetrahydrothiopyrane-2-one IV (9.26 g, 31.0 mmol) in THF (70 mL) was purged for 15 minutes with nitrogen. A degassed aqueous sodium hydroxide solution (2.2 M, 70 mL, 154 mmol) was added to the solution and the mixture was stirred at room temperature under nitrogen overnight. The reaction mixture was washed with ether, acidified by 3N HCl at 0° C., and extracted with ether. The extract was dried over MgSO4 and concentrated to afford 5-carboxy-2-chloro-alpha-(3-mercaptopropyl)benzenepropanoic acid 10 (8.42 g, 27.8 mmol, 90%) as a white solid: 1H NMR (CD3OD) δ 1.50–1.80 (m, 4H), 2.35–2.50 (m, 2H), 2.65–2.75 (m, 1H), 2.91 (dd, J=6.2, 13.8 Hz, 1H), 2.96 (dd, J=8.8, 13.8 Hz, 1H), 7.39 (d, J=8.3 Hz, 1H), 7.76 (dd, J=2.0, 8.3 Hz, 1H), 7.86 (d, J=2.0 Hz, 1H); 13C NMR (CD3OD) δ 25.1, 32.5, 33.2, 37.4, 46.8, 130.8, 131.2, 134.0, 139.1, 140.5, 169.2, 178.9. Anal. Calcd for C13H15ClO4S: C, 51.57; H, 4.99; S, 10.59; Cl, 11.71. Found: C, 51.59; H, 4.94; S, 10.43; Cl, 11.80.

Workup

  1. washThe reaction mixture was washed with ether
  2. customacidified by 3N HCl at 0° C.
  3. extractionextracted with ether
  4. dry with materialThe extract was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b9ad137aa2f04903babb80bbf947d6e7
Source dataset
uspto-grants-2006_01
Patent number
US06992215B2

Reaction notes

Loading…