Acetic Acid → HCID 18003373, compound

HRID 478966Notes

Reaction equation

HRID 478966 reaction equation
C(O)(=O)C.C([O:7][C:8](=[O:39])[CH:9]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[NH:38])[NH2:37])=[CH:32][CH:31]=1)[C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[CH:13]=[C:12]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)[C:11]=1[F:28])C.[Li+].[OH-].C(O)(=O)C>C1COCC1>[C:36]([C:33]1[CH:34]=[CH:35][C:30]([NH:29][CH:9]([C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[CH:13]=[C:12]([O:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[C:11]=2[F:28])[C:8]([OH:39])=[O:7])=[CH:31][CH:32]=1)(=[NH:37])[NH2:38]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 70005447HCID 70005447, compound

Product 1

HCID 18003373HCID 18003373, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 340 mg (RS)-(4-carbamimidoyl-phenylamino)-[5-ethoxy-2-fluoro-3-(1-methyl-piperidin-4-ylmethoxy)-phenyl]-acetic acid ethyl ester acetate in 5 ml THF was treated with 2.8 ml 1N LiOH and stirred at room temperature for 2 hours. The reaction mixture was neutralized with acetic acid and evaporated in vacuo. The residue was stirred in 1.5 ml of water. Suction filtration and drying gave 173 mg (RS)-(4-carbamimidoyl-phenylamino)-[5-ethoxy-2-fluoro-3-(1-methyl-piperidin-4-ylmethoxy)-phenyl]-acetic acid. Mp.: 232° C. Light brown solid. MS: 459 ([M+H]+).

Workup

  1. customevaporated in vacuo
  2. stirringThe residue was stirred in 1.5 ml of water
  3. filtrationSuction filtration
  4. customdrying

Sources & evidence

ORD record
ord-ba10d2a199e54c85bdc96cf034f08754
Source dataset
uspto-grants-2003_11
Patent number
US06642386B2

Reaction notes

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