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

HRID 1908628Notes

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][CH2:35][CH3:36])=[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].Cl.[C:45]1(C)C=CC=CC=1>>[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][CH2:35][CH3:36])=[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]([O:18][CH3:45])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 1140Toluene

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 669203404-((S)-2-{[5-(1-Ethoxycarbonyl-cyclobutoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-4-methoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester

Procedure

To 30 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, 2 ml of methanolic hydrochloric acid was added at RT and stirred for 3 h. Then, 10 ml of toluene was added and the solvents were removed under reduced pressure and the product was lyophilized to yield a white solid. Yield: 25 mg MS (ES+): m/e=614.

Workup

customthe solvents were removed under reduced pressure
customto yield a white solid

Sources & evidence

ORD record: ord-b1401476805641dc835bcd6b535d8e96
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598179B2

Reaction notes

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