Hydrochloric Acid → N-{(1S,2R)-1-(3,5-Difluoro-benzyl)-2-hydroxy-2-[(2R,4R)-4-(2-methoxy-phenoxy)-pyrrolidin-2-yl]-ethyl}-acetamide hydrochloride

HRID 732610Notes

Reaction equation

HRID 732610 reaction equation
[ClH:1].C(OC([N:9]1[CH2:13][C@H:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[CH2:11][C@@H:10]1[C@H:23]1[O:27]C(C)(C)[N:25]([C:30](=[O:32])[CH3:31])[C@H:24]1[CH2:33][C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[C:36]([F:41])[CH:35]=1)=O)(C)(C)C>O1CCOCC1>[ClH:1].[F:41][C:36]1[CH:35]=[C:34]([CH:39]=[C:38]([F:40])[CH:37]=1)[CH2:33][C@H:24]([NH:25][C:30](=[O:32])[CH3:31])[C@H:23]([OH:27])[C@H:10]1[CH2:11][C@@H:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[CH2:13][NH:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68817598(2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-(2-methoxy-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68816345N-{(1S,2R)-1-(3,5-Difluoro-benzyl)-2-hydroxy-2-[(2R,4R)-4-(2-methoxy-phenoxy)-pyrrolidin-2-yl]-ethyl}-acetamide hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add 4M hydrogen chloride in dioxane (3 mL) to (2R,4R)-2-[(4S,5S)-3-acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-(2-methoxy-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.061 g, 0.21 mmol). Stir 1 h and concentrate to give the title compound as a foam (0.05 g, 100%).

Workup

  1. concentrationconcentrate

Sources & evidence

ORD record
ord-7606401391b7481faf3bb06bc469dfe6
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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