Benzenesulfonyl chloride → HCID 14858911, compound

HRID 1074015Notes

Reaction equation

HRID 1074015 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.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH:37]1([NH:43][CH:44]2[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]2)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>[OH-].[Na+].C(#N)C>[CH:44]1([NH:43][CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]1.[C:27]1([S:33]([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]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 7582DicyclohexylamineHCID 312751,4-DioxaneHCID 1715626epsilon-(Benzyloxycarbonyl)-L-lysine

Product 1

HCID 14858911HCID 14858911, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

Nε -benzyloxycarbonyl-L-lysine (8.41 g, 30 mmole) was dissolved in 1N aqueous sodium hydroxide (30 ml), and dioxane (10 ml) solution of benzene sulfonyl chloride (5 30 g, 30 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 1.5 hours at room temperature and then insoluble matter was removed by filtration. The filtrate 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 1.5 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 acetonitrile (200 ml), and then dicyclohexylamine (5.43 g, 30 mmole) was added thereto with stirring, and thereby Nα -benzenesulfonyl-Nε -benzyloxycarbonyl-L-lysine dicyclohexylamine salt (13.21 g, 73.2%) was obtained.

Workup

  1. stirringThe mixture was further stirred for 1.5 hours at room temperature
  2. custominsoluble matter was removed by filtration
  3. washThe filtrate was washed with two 100 ml portions of diethyl ether
  4. additionTo the water layer, ethyl acetate (150 ml) was added
  5. customThe ethyl acetate layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe oily residue thus obtained
  9. stirringwith stirring

Sources & evidence

ORD record
ord-9314bd4f8ee4498da2ea1451f6ce536d
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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