Hydrochloric Acid → HCID 86634502, compound

HRID 1972331Notes

Reaction equation

HRID 1972331 reaction equation
[CH:1]1([NH:4][C:5](=[O:45])[C@@H:6]([OH:44])[C@@H:7]([NH:11][C:12]([C@@H:14]2[CH2:18][C@@H:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([N:32]4[CH:36]=[CH:35][CH:34]=[N:33]4)[CH:21]=3)[CH2:16][N:15]2C(OC(C)(C)C)=O)=[O:13])[CH2:8][CH2:9][CH3:10])[CH2:3][CH2:2]1.[ClH:46].COC(C)(C)C>CO>[Cl-:46].[CH:1]1([NH:4][C:5](=[O:45])[C@@H:6]([OH:44])[C@@H:7]([NH:11][C:12]([C@@H:14]2[CH2:18][C@@H:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([N:32]4[CH:36]=[CH:35][CH:34]=[N:33]4)[CH:21]=3)[CH2:16][NH2+:15]2)=[O:13])[CH2:8][CH2:9][CH3:10])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 57872113HCID 57872113, compound

Product 1

HCID 86634502HCID 86634502, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cooled solution (0-5° C.) of (2S,4R)-tert-butyl 2-((2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamoyl)-4-(7-methoxy-2-(1H-pyrazol-1-yl)quinolin-4-yloxy)pyrrolidine-1-carboxylate (3.0 g; 4.82 mmol) in methanol (10 mL) was added 17% methanolic hydrochloric acid (20 mL) dropwise. The reaction mixture was stirred at room temperature for 2 hours under nitrogen atmosphere. Completion of the reaction was monitored by TLC. Methyl t-butylether (50 mL) was added to the mixture and stirred for 10 minutes. The obtained solid was filtered and dried to yield 2.45 g (98%) of (2S,4R)-2-((2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamoyl)-4-(7-methoxy-2-(1H-pyrazol-1-yl)quinolin-4-yloxy)pyrrolidinium chloride (HPLC purity: 97.74% by area; HPLC retention time: 13.30 minutes), which was used without further purification in the next step.

Workup

  1. stirringstirred for 10 minutes
  2. filtrationThe obtained solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-32c063e47ab841e3acab262a1ed6f7e1
Source dataset
uspto-grants-2013_04
Patent number
US08431733B2

Reaction notes

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