Lithium hydroxide, monohydrate → (+/-)-2-[[5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2-oxo-4-thioxo-1(2H)-pyrimidinyl]methyl]-4-oxazolecarboxylic acid

HRID 324398Notes

Reaction equation

HRID 324398 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:9]=3[CH:8]([C:18]3[C:19](=[S:36])[NH:20][C:21](=[O:35])[N:22]([CH2:24][C:25]4[O:26][CH:27]=[C:28]([C:30]([O:32]CC)=[O:31])[N:29]=4)[CH:23]=3)[C:6]=2[N:7]=1)[CH3:2].O.[OH-].[Li+]>CO.O>[CH2:1]([C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:9]=3[CH:8]([C:18]3[C:19](=[S:36])[NH:20][C:21](=[O:35])[N:22]([CH2:24][C:25]4[O:26][CH:27]=[C:28]([C:30]([OH:32])=[O:31])[N:29]=4)[CH:23]=3)[C:6]=2[N:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 131722502(+/-)-2-[[5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2-oxo-4-thioxo-1(2H)-pyrimidinyl]methyl]-4-oxazolecarboxylic acid, ethyl ester

Product 1

HCID 9826263(+/-)-2-[[5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2-oxo-4-thioxo-1(2H)-pyrimidinyl]methyl]-4-oxazolecarboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of the product of step (ii) (0.55 g) and lithium hydroxide monohydrate (0.46 g) in methanol (10 ml) and water (10 ml) was stirred at room temperature for 3 hours. The solution was concentrated under reduced pressure to 10 ml and partitioned between 2M hydrochloric acid and ethyl acetate. The organic phase was dried (MgSO4) and the solvent evaporated under reduced pressure. Purification was by reverse phase chromatography eluting with 50% methanol in 0.1% aqueous ammonium acetate followed by lyophilisation.

Workup

  1. concentrationThe solution was concentrated under reduced pressure to 10 ml
  2. custompartitioned between 2M hydrochloric acid and ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customthe solvent evaporated under reduced pressure
  5. customPurification
  6. washeluting with 50% methanol in 0.1% aqueous ammonium acetate

Sources & evidence

ORD record
ord-aee5877d2d504d428cb653b45ca23e16
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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