Lithium Hydroxide → 3-[4-(1-tert-Butoxycarbonylamino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid

HRID 1037406Notes

Reaction equation

HRID 1037406 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[O:13][C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[C:11]([C:21]1[CH:26]=[CH:25][C:24]([C:27]3([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:29][CH2:28]3)=[CH:23][CH:22]=1)[C:10]2=[O:39])=[O:4].[OH-].[Li+]>C1COCC1.CCOC(C)=O>[C:35]([O:34][C:32]([NH:31][C:27]1([C:24]2[CH:23]=[CH:22][C:21]([C:11]3[C:10](=[O:39])[C:9]4[C:14](=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[CH:7][CH:8]=4)[O:13][C:12]=3[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:26][CH:25]=2)[CH2:28][CH2:29][CH2:30]1)=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67067838HCID 67067838, compound

Product 1

HCID 670678653-[4-(1-tert-Butoxycarbonylamino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid methyl ester (31 mg, 0.059 mmol) in THF (2 mL) was added a solution of 2 M aqueous lithium hydroxide (2 mL) and the reaction stirred at RT for 18 h. The reaction mixture was diluted with EtOAc, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound as an off-white solid (30 mg, 100%). LCMS (Method G): RT=3.81 min, [M+H]+=512.

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b5310bab0824061a5faa9ff234bd0ce
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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