Dicyclohexylamine → HCID 14858914, compound

HRID 1074017Notes

Reaction equation

HRID 1074017 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([OH:20])=[O:19])[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.[N+:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36](Cl)(=[O:38])=[O:37])([O-:29])=[O:28].[CH:40]1([NH:46][CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>[OH-].[Na+].C(OCC)C>[CH:47]1([NH:46][CH:40]2[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]2)[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]1.[N+:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36]([NH:17][C@H:16]([C:18]([OH:20])=[O:19])[CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])(=[O:38])=[O:37])([O-:29])=[O:28]

Participants

7

Reactant 4

HCID 7582DicyclohexylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 312751,4-DioxaneHCID 1715626epsilon-(Benzyloxycarbonyl)-L-lysine

Product 1

HCID 14858914HCID 14858914, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

Nε -benzyloxycarbonyl-L-lysine (4.42 g, 16 mmole) was dissolved in 1N aqueous sodium hydroxide (16 ml), and dioxane (10 ml) solution of o-nitrobenzene sulfonyl chloride (3.50 g, 16 mmole) was added dropwise to the solution while keeping the pH value thereof to between 10 and 11 with 1N aqueous sodium hydroxide while cooling with ice and stirring. The mixture was further stirred for 2.5 hours at room temperature, and insoluble matter was removed by filtration. The filtrate thus obtained was washed with two 100 ml portions of diethyl ether. To the water layer, ethyl acetate (150 ml) was added and the solution was adjusted to pH 1.0 with 1N aqueous hydrochloric acid under vigorous stirring. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the oily residue thus obtained was dissolved in diethyl ether (50 ml). To the solution, with stirring, dicyclohexylamine 2.99 g, 17 mmole) was added to obtain Nα -o-nitrobenzenesulfonyl-Nε -benzyloxycarbonyl-L-lysine dicyclohexylamine salt (yield:8.52 g; 83.4%)

Workup

  1. stirringThe mixture was further stirred for 2.5 hours at room temperature
  2. custominsoluble matter was removed by filtration
  3. customThe filtrate thus obtained
  4. washwas washed with two 100 ml portions of diethyl ether
  5. additionTo the water layer, ethyl acetate (150 ml) was added
  6. customThe ethyl acetate layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe oily residue thus obtained
  10. stirringTo the solution, with stirring

Sources & evidence

ORD record
ord-918581a1b64944e283ba2059b828fda3
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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