Hydrochloric Acid → HCID 69803643, compound

HRID 2179946Notes

Reaction equation

HRID 2179946 reaction equation
CC(O[C:6](=O)[N:7]([CH2:9][CH2:10][C@@H:11]([O:18][C:19]1[CH:24]=[C:23]([Cl:25])[C:22]([F:26])=[CH:21][C:20]=1[C:27]#[N:28])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C)(C)C.Cl.[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33]>O1CCOCC1.C(O)C>[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33].[Cl:25][C:23]1[C:22]([F:26])=[CH:21][C:20]([C:27]#[N:28])=[C:19]([O:18][C@@H:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:10][CH2:9][NH:7][CH3:6])[CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 971Oxalic AcidHCID 69798263HCID 69798263, compound

Product 1

HCID 69803643HCID 69803643, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

[(3R)-3-(5-Chloro-2-cyano-4-fluorophenoxy)-3-phenylpropyl]methyl carbamic acid 1,1-dimethylethyl ester (220 mg, 0.525 mmol) was stirred in a 4N solution of hydrogen chloride in dioxan (20 ml) for 20 minutes. The hydrochloride salt was,applied to a silica gel column and eluted with 10% 7N ammonia in methanol/dichloromethane. The free base was then converted into an oxalate salt with 1 equivalent of oxalic acid in ethanol. The title compound was obtained as a colourless solid (175 mg, 82%).

Workup

  1. washeluted with 10% 7N ammonia in methanol/dichloromethane

Sources & evidence

ORD record
ord-4f43cd7dc686468a9b79f279132ac829
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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