Hydrochloric Acid → 4-((S)-4-Carboxy-2-{[5-(1-carboxy-cyclobutoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester

HRID 1908602Notes

Reaction equation

HRID 1908602 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:43])[C@@H:13]([NH:19][C:20]([C:22]2[CH:26]=[C:25]([O:27][C:28]3([C:32]([O:34]CC)=[O:33])[CH2:31][CH2:30][CH2:29]3)[N:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:23]=2)=[O:21])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[OH-].[Na+].Cl>C1COCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:43])[C@@H:13]([NH:19][C:20]([C:22]2[CH:26]=[C:25]([O:27][C:28]3([C:32]([OH:34])=[O:33])[CH2:31][CH2:30][CH2:29]3)[N:24]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:23]=2)=[O:21])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 44126037(4S)-4-([5-[1-(ethoxycarbonyl)cyclobutoxy]-1-phenyl-1H-pyrazol-3-yl]formamido)-5-[4-(ethoxycarbonyl)piperazin-1-yl]-5-oxopentanoic acid

Product 1

HCID 441260384-((S)-4-Carboxy-2-{[5-(1-carboxy-cyclobutoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 70 mg of 4-((S)-4-Carboxy-2-{[5-(1-ethoxycarbonyl-cyclobutoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester in 2 ml of THF, 0.3 ml of a 1 M aqueous NaOH solution was added. After stirring for 1 h at RT additional 0.3 ml of a 1 M aqueous NaOH solution was added and allowed to stir upon completion of the reaction. Then, the reaction was acidified to pH 1 with diluted aqueous hydrochloric acid and extracted with DCM (3×50 ml). The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure. Yield: 49 mg MS (ES+): m/e=572.

Workup

  1. additionwas added
  2. extractionextracted with DCM (3×50 ml)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-739b36ee70af48728a6fd34b22c6d52a
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

Loading…