HCID 18789771, compound → HCID 54465196, compound

HRID 1106657Notes

Reaction equation

HRID 1106657 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][C:8]([C:17]#[N:18])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][CH3:10].[N+](C1C=CC([O:28][C:29]([N:31]2[CH:35]([C:36]3[CH:41]=[C:40]([F:42])[C:39]([F:43])=[C:38]([F:44])[CH:37]=3)[CH2:34][O:33][C:32]2=[O:45])=O)=CC=1)([O-])=O>C1COCC1>[C:17]([C:8]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:9][CH2:10][CH:5]([NH:4][CH2:3][CH2:2][NH:1][C:29]([N:31]2[CH:35]([C:36]3[CH:41]=[C:40]([F:42])[C:39]([F:43])=[C:38]([F:44])[CH:37]=3)[CH2:34][O:33][C:32]2=[O:45])=[O:28])[CH2:6][CH2:7]1)#[N:18]

Participants

4

Reactant 2

HCID 18789771HCID 18789771, compoundHCID 22048993HCID 22048993, compound

Product 1

HCID 54465196HCID 54465196, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[(2-amino-ethyl)-amino]-4-cyano-4-phenylhexane (25 mg, 0.103 mmol) in 10 mL of THF, 4-(3,4,5-trifluorophenyl)-2-oxo-oxazolidine-3-carboxylic acid-4-nitro-phenyl ester (30 mg, 0.079 mmol) was added and the resulting yellow solution was stirred under argon atmosphere for 2 h at room temperature. The solvent was removed in vacuo and the residue was purified by column chromatography over silica gel with 1:1 hexane/EtOAc followed by MeOH:EtOAc=1:9 (Rf =0.60, MeOH:EtOAc=1:3) to obtain the title compound. The compound was dissolved in CH2Cl2 (3 mL) and was treated with 1N HCl in ether (1 mL). The solvent was removed in vacuo to give the corresponding hydrochloride salt as a pale yellow solid. M. P. 130-134° C.; [α]D =+43.5, (c=0.25, MeOH); Anal. Calcd. For C25H26N4O3F3Cl 1.10 C3H6O: C, 57.92; H, 5.60; N, 8.55. Found: C, 58.33; H, 5.90; N, 8.52.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography over silica gel with 1:1 hexane/EtOAc

Sources & evidence

ORD record
ord-e8c226a325a3479a97e044ff7de21f1a
Source dataset
uspto-grants-2000_05
Patent number
US06057350

Reaction notes

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