Hydrochloric Acid → HCID 10309647, compound

HRID 857281Notes

Reaction equation

HRID 857281 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:19]=[C:20]([CH:28]([CH3:30])[CH3:29])[CH:21]=[C:22]4[C:27]=3[N:26]=[CH:25][CH:24]=[CH:23]4)[CH:13]=2)=[CH:6][CH:5]=1.[Li+].[OH-].Cl>C1COCC1.CO>[CH:28]([C:20]1[CH:21]=[C:22]2[C:27](=[C:18]([C:14]3[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=3)[O:11][CH2:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=3)[CH:19]=1)[N:26]=[CH:25][CH:24]=[CH:23]2)([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10194461HCID 10194461, compound

Product 1

HCID 10309647HCID 10309647, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the ester of EXAMPLE 9 (1.0 eq) in THF/MeOH (2/1; 0.1M) was added of aqueous solution of LiOH (1N; 5.0 eq). The resulting mixture was stirred 1 hour at 70° C., acidified to pH 5 using HCl (1N) and extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9:1 to 1:9 in 15 min) afforded the title compound as a white solid.

Workup

  1. extractionextracted with Et2O (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5430998f71714d259a4660b3e952526e
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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