Sodium Hydroxide → HCID 178439174, compound

HRID 1809970Notes

Reaction equation

HRID 1809970 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([CH2:21][C:22]2[O:26][C:25]([C:27]([O:29]CC)=[O:28])=[CH:24][CH:23]=2)[NH:7][C:8]=1[NH:9][C:10](=[O:20])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH3:19])=[CH:13][CH:12]=1)(=[O:3])[NH2:2].C(O)C.C1COCC1.[OH-].[Na+]>C(O)(=O)C>[C:1]([C:4]1[N:5]=[C:6]([CH2:21][C:22]2[O:26][C:25]([C:27]([OH:29])=[O:28])=[CH:24][CH:23]=2)[NH:7][C:8]=1[NH:9][C:10](=[O:20])[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][CH3:19])=[CH:15][CH:16]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21873804Tetrahydrofuran ethanolHCID 178439173HCID 178439173, compound

Product 1

HCID 178439174HCID 178439174, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

1.8 g (4.24 mM) of ethyl 5-[4-carbamoyl-5-(4-propylbenzoylamino)-1H-imidazol-2-ylmethyl]furan-2-carboxylate are added to 10 ml of an ethanol/THF mixture (50-50). 4 ml of aqueous 3N sodium hydroxide solution are then added and the reaction medium is maintained at 40° C. with stirring for 2 hours. The reaction medium is allowed to cool and is acidified with acetic acid; a solid crystallizes. The solid is filtered off and washed with demineralized water to give, after drying, 1.7 g of 5-[4-carbamoyl-5-(4-propylbenzoylamino)-1H-imidazol-2-ylmethyl]furan-2-carboxylic acid.

Workup

  1. temperatureto cool
  2. customa solid crystallizes
  3. filtrationThe solid is filtered off
  4. washwashed with demineralized water
  5. customto give
  6. customafter drying

Sources & evidence

ORD record
ord-6c36c6e0d69c4f6aa4173c0dbf6c59a1
Source dataset
uspto-grants-2013_01
Patent number
US08362057B2

Reaction notes

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