Propane sultone → 4-iodo-N-(3-sulfopropyl)-L-phenylalanine amide

HRID 2219722Notes

Reaction equation

HRID 2219722 reaction equation
[I:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][C@@H:7]([C:9]([NH2:11])=[O:10])[NH2:8])=[CH:4][CH:3]=1.[CH2:14]1[CH2:20][S:17](=[O:19])(=[O:18])[O:16][CH2:15]1>CC(=O)CC.CN(C=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]([C:9]([NH:11][CH2:15][CH2:14][CH2:20][S:17]([OH:19])(=[O:18])=[O:16])=[O:10])[NH2:8])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 14264Propane sultoneHCID 447705(S)-2-Amino-3-(4-iodophenyl)propanamide

Product 1

HCID 1317270024-iodo-N-(3-sulfopropyl)-L-phenylalanine amideYield 17.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

The amide (1.3 g, 4.4 mmol) was dissolved in 15 mL of 2-butanone with a few drops of DMF before 1,3-propane sultone (560 mg, 4.9 mmol) was added. The reaction mixture was stirred at reflux for 2 hours. The mixture was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×20 mL) and dried in vacuo. The solid was suspended in MeOH (25 mL) and a small amount of water (1 mL). The suspension was stirred at reflux. The solid material was collected by filtration while the mixture was still hot. The solid was washed with hot MeOH (2×10 mL). Compound CO was obtained as a white solid (320 mg).

Workup

  1. additionwas added
  2. temperatureat reflux for 2 hours
  3. filtrationThe solid was collected by filtration
  4. washwashed with acetone (2×20 mL)
  5. customdried in vacuo
  6. stirringThe suspension was stirred
  7. temperatureat reflux
  8. filtrationThe solid material was collected by filtration while the mixture
  9. washThe solid was washed with hot MeOH (2×10 mL)

Sources & evidence

ORD record
ord-cf6520a78c6b429fb8da64d99316dbd7
Source dataset
uspto-grants-2008_08
Patent number
US07414076B2

Reaction notes

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