(2R, 5S)-(5-Chloro-2-[2-[4-(4-fluoro-benzyl)-2.5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-carbamic acid 4-nitro-phenyl Ester → HCID 12112109, compound

HRID 480189Notes

Reaction equation

HRID 480189 reaction equation
[N+](C1C=CC(O[C:11](=[O:40])[NH:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:21][C:22]([N:24]2[CH2:29][C@H:28]([CH3:30])[N:27]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[CH2:26][C@H:25]2[CH3:39])=[O:23])=CC=1)([O-])=O>CO>[NH2:24][CH2:25][CH2:26][NH:27][C:11]([NH:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[O:20][CH2:21][C:22]([N:24]1[CH2:29][C@H:28]([CH3:30])[N:27]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=2)[CH2:26][C@H:25]1[CH3:39])=[O:23])=[O:40]

Participants

3

Reactant 1

HCID 86585615(2R, 5S)-(5-Chloro-2-[2-[4-(4-fluoro-benzyl)-2.5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-carbamic acid 4-nitro-phenyl Ester

Product 1

HCID 12112109HCID 12112109, compoundYield 126.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2R, 5S)-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-carbamic acid 4-nitro-phenyl ester (0.206 g, 0.37 mmol) in dry methanol (6 ml) was added ethyldiamine (0.05 ml, 0.814 mmol). The reaction was stirred at ambient temperature overnight. The reaction was concentrated and chromatagraphed on silica gel to give the title compound (0.115 g, 63% yield).

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-6ff3e15c6a624fb49b256eada1ead0ce
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

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