Hydrochloric Acid → (+/-)-5-[[5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-2-furancarboxylic acid

HRID 324395Notes

Reaction equation

HRID 324395 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](=[O:36])[NH:20][C:21](=[O:35])[N:22]([CH2:24][C:25]4[O:29][C:28]([C:30]([O:32]CC)=[O:31])=[CH:27][CH:26]=4)[CH:23]=3)[C:6]=2[N:7]=1)[CH3:2].O.[OH-].[Li+].Cl>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](=[O:36])[NH:20][C:21](=[O:35])[N:22]([CH2:24][C:25]4[O:29][C:28]([C:30]([OH:32])=[O:31])=[CH:27][CH:26]=4)[CH:23]=3)[C:6]=2[N:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 131722500(+/-)-5-[[5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-2-furancarboxylic acid, ethyl ester

Product 1

HCID 9804236(+/-)-5-[[5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-2-furancarboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of the product of step (viii) (0.26 g) and lithium hydroxide monohydrate (0.063 g) in methanol (4 ml) and water (4 ml) was stirred at room temperature for 1.5 hours. The solution was neutralised by the addition of 2M hydrochloric acid and the solvents were evaporated under reduced pressure. Purification was by preparative HPLC followed by lyophilisation.

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. customPurification

Sources & evidence

ORD record
ord-47183b5df1f4426da8ee80d17122a7c0
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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