Sodium Hydroxide → HCID 14403487, compound

HRID 1195003Notes

Reaction equation

HRID 1195003 reaction equation
C[O:2][C:3]([CH:5]1[N:10]([C:11](=[O:25])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C:8]2[N:26]=[CH:27][N:28]([CH2:29][CH2:30][C:31]34[CH2:40][CH:35]5[CH2:36][CH:37]([CH2:39][CH:33]([CH2:34]5)[CH2:32]3)[CH2:38]4)[C:7]=2[CH2:6]1)=[O:4].[OH-].[Na+]>O1CCCC1CO>[C:31]12([CH2:30][CH2:29][N:28]3[C:7]4[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[N:10]([C:11](=[O:25])[CH:12]([C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=5)[C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=5)[CH2:9][C:8]=4[N:26]=[CH:27]3)[CH2:40][CH:35]3[CH2:36][CH:37]([CH2:39][CH:33]([CH2:34]3)[CH2:32]1)[CH2:38]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14403486HCID 14403486, compound

Product 1

HCID 14403487HCID 14403487, compound

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

A solution of 2.0 g methyl-1-(2-(1-adamantyl)ethyl)-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]-pyridine-6-carboxylate in tetrahydrofuranmethanol (3:1, 20 mL) is treated at 25° C. with 4.1 mL 1N NaOH. After 6 hr the solution is evaporated, the residue is suspended in 10 mL water and treated with 4.1 mL 1N HCl. The resulting precipitate is collected by filtration and dried to afford a white solid, 1(2-(1-adamantyl)ethyl)-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid. MS (FAB) 524 (M+1). mp 168°-175° C. or 187° to 200° C. dec.

Workup

  1. customAfter 6 hr the solution is evaporated
  2. additiontreated with 4.1 mL 1N HCl
  3. filtrationThe resulting precipitate is collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-47f4df2677824fb5ad8177685398a6fd
Source dataset
uspto-grants-1989_03
Patent number
US04816463

Reaction notes

Loading…