Hydrochloric Acid → HCID 57987555, compound

HRID 1869756Notes

Reaction equation

HRID 1869756 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([CH:12]([CH2:17][CH2:18][CH3:19])[C:13]([O:15]C)=[O:14])[C@@H:7]1[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1.[Li+].[OH-].O1CCOCC1.Cl>C1COCC1.O>[F:39][C:2]([F:1])([F:38])[C:3]1[CH:33]=[CH:32][C:31]([C:34]([F:35])([F:37])[F:36])=[CH:30][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([CH:12]([CH2:17][CH2:18][CH3:19])[C:13]([OH:15])=[O:14])[C@@H:7]1[C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 57987487HCID 57987487, compound

Product 1

HCID 57987555HCID 57987555, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of the ester from Step 1 (0.098 g, 0.17 mmol) and LiOH (0.082 g, 3.4 mmol) in THF (3 ml) and water (3 ml) was heated at 60° C. for 16 hrs. Then dioxane (3 ml) was added and the reaction was heated at 100° C. for 16 hrs. The reaction mixture was acidified to pH6 with 2N HCl and extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (silica, 1-2% MeOH/DCM) to give the acid (0.070 g, 74%). 1H NMR (400 MHz, CD3OD): δ 0.84 (3H, t, J 7.2), 0.86-0.97 (1H, m), 1.21-1.47 (3H, m), 1.61-1.83 (5H, m), 2.17 (1H, dt, J 3.0, 11.7), 2.28-2.34 (1H, m), 2.83 (1H, d, J 11.6), 3.37-3.57 (3H, m), 7.65 (5H, m), 7.75 (1H, d, J 8.2), 8.19 (1H, s).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (silica, 1-2% MeOH/DCM)

Sources & evidence

ORD record
ord-ddf4cb212d914045b5f7d86051ca3cd8
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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