Triethylamine → HCID 178470716, compound

HRID 2293626Notes

Reaction equation

HRID 2293626 reaction equation
FC(F)(F)C(O)=O.[N+:8]([NH:11][C:12](=[NH:33])[NH:13][CH2:14][CH2:15][CH2:16][C@@H:17]([C:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:23][CH2:22]1)=[O:20])[NH2:18])([O-:10])=[O:9].C(N(CC)CC)C.[CH3:41][C:42]([C:50]1[CH:51]=[C:52]([S:56](Cl)(=[O:58])=[O:57])[CH:53]=[CH:54][CH:55]=1)([CH3:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(Cl)Cl>[CH3:49][C:42]([C:50]1[CH:51]=[C:52]([S:56]([NH:18][C@H:17]([C:19]([N:21]2[CH2:26][CH2:25][CH:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:23][CH2:22]2)=[O:20])[CH2:16][CH2:15][CH2:14][NH:13][C:12](=[NH:33])[NH:11][N+:8]([O-:10])=[O:9])(=[O:57])=[O:58])[CH:53]=[CH:54][CH:55]=1)([CH3:41])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10637600HCID 10637600, compoundHCID 178470718HCID 178470718, compound

Product 1

HCID 178470716HCID 178470716, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
20 °C

Procedure

The above 1-((S)-Nω -nitroarginyl)-4-(ethoxycarbonylmethyl)piperidine trifluoroacetate (2.1 g) is suspended in dry CH2Cl2 (50 ml) and stirred at 0° to 5° C. during the addition of triethylamine (1.3 g) to give a solution. To this solution is added dropwise at 0°-5° C. a solution of 3-(α,α-dimethylbenzyl)benzenesulphonyl chloride (1.2 g) in dry CH2Cl2 (5 ml) and the reaction mixture is then stirred at 20° C. for 3 hours. The reaction mixture is then diluted by addition of CH2Cl2 (50 ml), washed with brine (3×150 ml) and the organic layer is dried (MgSO4) and concentrated by evaporation to give a solid residue which is purified by chromatography on silica gel using ethylacetate/methanol (9:1) as eluant. Thus is obtained 1-(Nα -(3-(α,α-dimethylbenzyl)benzenesulphonyl)-(S)-Nω -nitroarginyl)-4-(ethoxycarbonylmethyl)piperidine as a pale yellow oil, Rf (EtOH)=0.21.

Workup

  1. customto give a solution
  2. washwashed with brine (3×150 ml)
  3. dry with materialthe organic layer is dried (MgSO4)
  4. concentrationconcentrated by evaporation
  5. customto give a solid residue which
  6. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-404a209ae93f42e2adab977dc618c751
Source dataset
uspto-grants-1997_11
Patent number
US05686564

Reaction notes

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