Propane sultone → 3-{[(1S)-1-benzyl-2-(benzyloxy)-2-oxoethyl]amino}propane-1-sulfonic acid

HRID 239758Notes

Reaction equation

HRID 239758 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[C@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]1[CH2:26][S:23](=[O:25])(=[O:24])[O:22][CH2:21]1>O1CCOCC1>[CH2:12]([C@H:10]([NH:11][CH2:21][CH2:20][CH2:26][S:23]([OH:25])(=[O:24])=[O:22])[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 736312Benzyl 3-phenyl-L-alaninate

Product 1

HCID 870953533-{[(1S)-1-benzyl-2-(benzyloxy)-2-oxoethyl]amino}propane-1-sulfonic acidYield 46.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of L-Phenylalanine benzylester (1.8 g, 6.8 mmol) in 1,4-dioxane (10 mL) was added 1,3-propanesultone (708 mg, 6.5 mmol). The solution was stirred at reflux. After 1 hour, 20 mL of 1,4-dioxane was added to allow for good stiffing. The reaction was stirred at reflux for an additional 1 hour. It was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×25 mL). The product was suspended 80% Acetone/EtOH. The suspension was stirred at reflux for 30 seconds. The solid was filtered and dried in the vacuum oven (50° C.) affording the title compound (1.14 g, 46%). 1H NMR (DMSO, 500 MHz) δ ppm 7.27 (m, 6H), 7.12 (m, 4H), 5.05 (dd, 2H, J=12.3 Hz), 4.49 (m, 1H). 3.29 (m, 1H), 3.00 (m, 1H), 2.98 (m, 1H), 2.61 (t, 2H, J=6.5 Hz), 1.97 (m, 2H). 13C (DMSO, 125 MHz) δ ppm 168.88, 135.21, 134.90, 130.00, 129.31, 129.07, 128.01, 67.98, 60.50, 49.77, 46.72, 35.87, 22.43. [α]D=+4.8° (c=0.00073 in water), ES-MS 378 (M+1).

Workup

  1. temperatureat reflux
  2. stirringThe reaction was stirred
  3. temperatureat reflux for an additional 1 hour
  4. filtrationThe solid was collected by filtration
  5. washwashed with acetone (2×25 mL)
  6. stirringThe suspension was stirred
  7. temperatureat reflux for 30 seconds
  8. filtrationThe solid was filtered
  9. customdried in the vacuum oven (50° C.)

Sources & evidence

ORD record
ord-3b95d8ecfdef4eea870bb777e2a1bffe
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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