Sodium Hydroxide → 3-Benzyloxy-5-(4-fluorobenzyl)-4-oxo-7-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylic acid

HRID 1453830Notes

Reaction equation

HRID 1453830 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:25]([O:27]C)=[O:26])=[N:11][N:12]2[CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:16][NH:15][C:14](=[O:24])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Br)=[CH:32][CH:31]=1.[OH-].[Na+]>>[CH2:1]([O:8][C:9]1[C:10]([C:25]([OH:27])=[O:26])=[N:11][N:12]2[CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:16][N:15]([CH2:34][C:33]3[CH:36]=[CH:37][C:30]([F:29])=[CH:31][CH:32]=3)[C:14](=[O:24])[C:13]=12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromideHCID 68951327Methyl 3-benzyloxy-4-oxo-7-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

Product 1

HCID 688930003-Benzyloxy-5-(4-fluorobenzyl)-4-oxo-7-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylic acid

Procedure

The title compound was prepared from methyl 3-benzyloxy-4-oxo-7-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate using a procedure similar to that described in Example 2, Step 4, except that 4-fluorobenzyl bromide was used in place of iodomethane, and 1N aqueous NaOH was used to quench the reaction and saponify the ester. ES MS (M+1)=472.

Workup

  1. customto quench
  2. customthe reaction

Sources & evidence

ORD record
ord-5bdf03190fc0496d99a67e81ddfcf905
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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