Iodoethane → HCID 54148847, compound

HRID 1746593Notes

Reaction equation

HRID 1746593 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]([C:22]([OH:24])=[O:23])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].I[CH2:26][CH3:27]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:3]([O:7][C:8]([NH:10][C@H:11]([C:22]([OH:24])=[O:23])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:26][CH3:27])[CH:14]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 83169N-tert-Butoxycarbonyl-L-tryptophan

Product 1

HCID 54148847HCID 54148847, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium hydroxide (4.6 g) was finely divided in an argon atmosphere, and thereafter methylene chloride (160 mL), N-tert-butoxycarbonyl-L-tryptophan (10.0 g), iodoethane (13.2 mL), and tetra-n-butylammonium hydrogensulfate (1.1 g) was added thereto, and the mixture was stirred for 64 hours at room temperature. The reaction mixture was washed with a 10% aqueous citric acid solution and saturated sodium chloride solution, and thereafter the organic layer was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under a reduced pressure was purified with silica gel column chromatography (chloroform:methanol=200:1), to give the captioned compound (5.7 g, 52%) as an oily product.

Workup

  1. washThe reaction mixture was washed with a 10% aqueous citric acid solution and saturated sodium chloride solution
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customThe residue obtained
  4. distillationby distilling off the solvent under a reduced pressure
  5. customwas purified with silica gel column chromatography (chloroform:methanol=200:1)

Sources & evidence

ORD record
ord-5080677a68fb4a538679f77d054bbef9
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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