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Hydrochloric Acid → N-(2-hydroxyethyl)-N-{[1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-yl]carbonyl}glycine

HRID 1364236
Notes
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Reaction equation

HRID 1364236 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([C:13]([C:15]1[CH:16]=[N:17][N:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][C@H:31]3[CH3:35])=[CH:22][CH:21]=2)[CH:19]=1)=[O:14])[CH2:5][C:6]([O:8]C(C)(C)C)=[O:7].Cl>O1CCOCC1.C(OCC)(=O)C>[OH:1][CH2:2][CH2:3][N:4]([C:13]([C:15]1[CH:16]=[N:17][N:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][C@H:31]3[CH3:35])=[CH:22][CH:21]=2)[CH:19]=1)=[O:14])[CH2:5][C:6]([OH:8])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 42610556tert-butyl N-(2-hydroxyethyl)-N-{[1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-yl]carbonyl}glycinate

Product 1

HCID 42610557N-(2-hydroxyethyl)-N-{[1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-yl]carbonyl}glycineYield 38.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent
HCID 31275
1,4-Dioxane
Solvent

Procedure

To a solution of tert-butyl N-(2-hydroxyethyl)-N-{[1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-yl]carbonyl}glycinate prepared in Example 67-(3) (0.218 g) in 1,4-dioxane (4.0 ml), a solution of hydrochloric acid in ethyl acetate (4 M, 4.0 ml) was added and stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by octadecylsilyl (ODS) column chromatography (eluting solvent: acetonitrile:water=95:5) to give the titled compound (0.075 g) as a colorless amorphous substance.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by octadecylsilyl (ODS) column chromatography (eluting solvent: acetonitrile:water=95:5)

Sources & evidence

ORD record
ord-135d0e52e04a4d75aa4f070ff7a52ed7
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07888354B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes