Lithium Hydroxide → HCID 54567229, compound

HRID 399072Notes

Reaction equation

HRID 399072 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:33]=[CH:34][CH:35]=1)[CH2:8][O:9][N:10]=[C:11]1[C:14]([CH3:16])([CH3:15])[C:13]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[C:12]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([O:3]C)=[O:2].[Li+].[OH-]>C1COCC1.CO.CCOC(C)=O.Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH:33]=[CH:34][CH:35]=1)[CH2:8][O:9][N:10]=[C:11]1[C:14]([CH3:15])([CH3:16])[C:13]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[C:12]1[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([OH:3])=[O:2]

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 53988182HCID 53988182, compound

Product 1

HCID 54567229HCID 54567229, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl ester from Example 52 (90 mg) in THF (2 mL) and MeOH (1 mL) was treated with LiOH (2N, 276 μL ). The mixture was heated at reflux for 18 hr, cooled to r.t. and diluted with EtOAc and HCl 1N. The organic phase was washed with brine, dried (MgSO4) and the solvent evaporated to give the title compound as white foam; 1H NMR (300 MHz, Ace-d6): δ 1.64 (s,6H), 3.17 (s, 3H), 5.26 (s, 2H), 7.39 (m, 3H), 7.51 (t, 1H), 7.70 (m, 3H),7.86 (d, 2H), 8.0 (m, 3H), 8.15 (br s, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hr
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-fa51dba187fb4ee099e85055d657bc4b
Source dataset
uspto-grants-1998_10
Patent number
US05817700

Reaction notes

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