HCID 86608357, compound → N-(3-Sulfopropyl)-L-phenylalanine

HRID 239774Notes

Reaction equation

HRID 239774 reaction equation
C([O:3][C:4](=[O:21])[C@H:5]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:6][CH2:7][CH2:8][CH2:9][S:10]([OH:13])(=[O:12])=[O:11])C>[OH-].[Na+]>[C:15]1([CH2:14][C@H:5]([NH:6][CH2:7][CH2:8][CH2:9][S:10]([OH:13])(=[O:11])=[O:12])[C:4]([OH:21])=[O:3])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 1

HCID 86608357HCID 86608357, compound

Product 1

HCID 16036063N-(3-Sulfopropyl)-L-phenylalanineYield 84.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The N-(3-sulfo-propyl)-phenylalanine ethyl ester (DM-258-069, 860 mg, 2.7 mmol) was dissolved in 2N NaOH (1.2 g of NaOH and 15 mL of water). The reaction was stirred at room temperature overnight. Dowex Marathon C ion exchange resin (strongly acidic) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated under reduced pressure and lyophilized, affording the title compound (654 mg, 84%). 1H NMR (D2O, 500 MHz) δ ppm 7.20 (m, 5H), 3.96 (t, 1H, J=6.3 Hz), 3.11 (m, 4H), 2.80 (t, 2H, J=7.3 Hz), 1.95 (m, 2H). 13C (D2O, 125 MHz) δ ppm 171.46, 134.03, 129.50, 129.28, 128.10, 62.02, 47.97, 45.64, 35.23, 21.39. [α]D=+14.9° (c=0.0013 in water), ES-MS 286 (M−1).

Workup

  1. additionDowex Marathon C ion exchange resin (strongly acidic) was added to the solution
  2. stirringThe suspension was stirred for 15 minutes before the resin
  3. customwas removed by filtration
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5e9c469b201f49d184212e5f19920cd2
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

Loading…