Propane sultone → 3-{[(1S)-2-tert-butoxy-1-methyl-2-oxoethyl]amino}-1-propanesulfonic acid

HRID 239772

Reaction equation

HRID 239772 reaction equation
[C:1]([O:5][C:6](=[O:10])[C@H:7]([CH3:9])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH2:11]1[CH2:17][S:14](=[O:16])(=[O:15])[O:13][CH2:12]1>O1CCCC1>[C:1]([O:5][C:6](=[O:10])[C@@H:7]([NH:8][CH2:12][CH2:11][CH2:17][S:14]([OH:16])(=[O:15])=[O:13])[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 89016L-Alanine 1,1-dimethylethyl ester

Product 1

HCID 160360613-{[(1S)-2-tert-butoxy-1-methyl-2-oxoethyl]amino}-1-propanesulfonic acidYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of L-Alanine tert-butylester (1.53 g, 10.5 mmol) in tetrahydrofuran (20 mL) was added 1,3-propanesultone (1.16 g, 9.6 mmol). The solution stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration and washed with acetone (2×20 mL). The solid was dissolved in water (80 mL). 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. The solid was suspended in acetone (80 mL), filtered and dried in the vacuum oven (50° C.), affording the title compound (1.37 g, 54%). 1H NMR (D2O, 500 MHz) δ ppm 3.88 (m, 1H), 3.09 (m, 2H), 2.86 (t, 2H, J=7.3 Hz), 2.00 (m, 2H), 1.39 (d, 3H, J=7.3 Hz), 1.35 (s, 9H). 13C (D2O, 125 MHz) δ ppm 169.13, 86.12, 56.24, 47.94, 44.71, 27.11, 21.52, 14.17. [α]D=−1.1° (c=0.0027 in water), ES-MS 266 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×20 mL)
  4. dissolutionThe solid was dissolved in water (80 mL)
  5. additionDowex Marathon C ion exchange resin (strongly acidic) was added to the solution
  6. stirringThe suspension was stirred for 15 minutes before the resin
  7. customwas removed by filtration
  8. customThe filtrate was evaporated under reduced pressure
  9. filtrationfiltered
  10. customdried in the vacuum oven (50° C.)

Sources & evidence

ORD record
ord-4546b68b7e9e4606a04b55abd139f7a0
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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