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

HRID 732612Notes

Reaction equation

HRID 732612 reaction equation
[ClH:1].C(OC([N:9]1[CH2:13][C@H:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=2)[CH2:11][C@@H:10]1[C@H:27]1[O:31]C(C)(C)[N:29]([C:34](=[O:36])[CH3:35])[C@H:28]1[CH2:37][C:38]1[CH:43]=[C:42]([F:44])[CH:41]=[C:40]([F:45])[CH:39]=1)=O)(C)(C)C>O1CCOCC1>[ClH:1].[F:45][C:40]1[CH:39]=[C:38]([CH:43]=[C:42]([F:44])[CH:41]=1)[CH2:37][C@H:28]([NH:29][C:34](=[O:36])[CH3:35])[C@H:27]([OH:31])[C@H:10]1[CH2:11][C@@H:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=2)[CH2:13][NH:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68817268(2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-(3-trifluoromethoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86615018N-{(1S,2R)-1-(3,5-Difluoro-benzyl)-2-hydroxy-2-[(2R,4R)-4-(3-trifluoromethoxy-benzyloxy)-pyrrolidin-2-yl]-ethyl}-acetamide hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add 4M hydrogen chloride in dioxane (5 mL) to (2R,4R)-2-[(4S,5S)-3-acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-(3-trifluoromethoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.138 g, 0.22 mmol). Stir 18 h and concentrate to give the title compound as a foam (0.11 g, 100%).

Workup

  1. concentrationconcentrate

Sources & evidence

ORD record
ord-3f127e93b1ee4292a2106ffc20276dc8
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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