Hydrochloric Acid → HCID 53655601, compound

HRID 861691Notes

Reaction equation

HRID 861691 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[O:12][C:11]2[CH:13]=[C:14]([CH:17]([OH:25])[CH2:18][CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[CH:15]=[CH:16][C:10]=2[O:9]1.[OH-].[Li+].Cl>O.C1COCC1>[OH:25][CH:17]([C:14]1[CH:15]=[CH:16][C:10]2[O:9][CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:26])=[O:2])[O:12][C:11]=2[CH:13]=1)[CH2:18][CH2:19][C:20]1[S:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 18972191HCID 18972191, compound

Product 1

HCID 53655601HCID 53655601, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

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-465e3157728d4d8d84410fede25d4af1
Source dataset
uspto-grants-1998_02
Patent number
US05714621

Reaction notes

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