Hydrochloric Acid → HCID 53655601, compound

HRID 363479Notes

Reaction equation

HRID 363479 reaction equation
[OH:1][CH:2]([C:10]1[CH:11]=[CH:12][C:13]2[O:17][CH:16]([CH:18]([CH2:22][CH2:23][CH3:24])C([O-])=O)[O:15][C:14]=2[CH:25]=1)[CH2:3][CH2:4][C:5]1[S:6][CH:7]=[CH:8][CH:9]=1.[OH-:26].[Li+].Cl.C1[CH2:33][O:32]CC1>O>[OH:1][CH:2]([C:10]1[CH:11]=[CH:12][C:13]2[O:17][CH:16]([CH2:18][CH2:22][CH2:23][CH2:24][C:33]([OH:32])=[O:26])[O:15][C:14]=2[CH:25]=1)[CH2:3][CH2:4][C:5]1[S:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 131721130HCID 131721130, compound2×

Product 1

HCID 53655601HCID 53655601, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of (±)-methyl-5-[[6-(1-hydroxy-3-(2-thienyl)propyl-1,3-benzodioxolyl]pentanoate (Compound F. 35 mg, 0.093 mmol) and lithium hydroxide (0.37 mL of a 0.5N solution in H2O, 0.186 mmol) in THF (0.74 mL) was stirred at 23° C. for 16 hours. The mixture was acidified with 1N HCl and extracted with EtOAc. The organic portion was dried (MgSO4) filtered and concentrated in vacuo. Flash column chromatography (silica gel, 100% EtOAc) afforded 33.3 mg (99%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 12.0 (brs, 1H), 7.14 (d, J=5. 1 Hz, 1H), 7.00 (s, 1H), 6.93 (dd, J=3.3, 5.1 Hz, 1H), 6.83 (d, J=3.3 Hz, 1H), 6.59 (s,1H), 5.91 (s, 2H), 4.87-4.92 (m, 1H), 2.97 (t, J=5.4 Hz, 2H), 2.43-2.47 (m,2H), 2.32 (t, J=6.9 Hz, 2H), 1.86-2.18 (m, 2H), 1.44-1.64 (m, 5H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2841ea22dc84480a9a4ff351e52da777
Source dataset
uspto-grants-1999_02
Patent number
US05874460

Reaction notes

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