Propane sultone → HCID 58931799, compound

HRID 239780

Reaction equation

HRID 239780 reaction equation
[NH2:1][C@@H:2]([C:10]([NH2:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:13]1[CH2:19][S:16](=[O:18])(=[O:17])[O:15][CH2:14]1>C(#N)C>[C:10]([C@H:2]([NH:1][CH2:14][CH2:13][CH2:19][S:16]([OH:18])(=[O:17])=[O:15])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:11])[NH2:12]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 7000171(2R)-2-amino-3-phenylpropanamide

Product 1

HCID 58931799HCID 58931799, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of D-Phenylalaninamide (1.83 g, 11.1 mmol) in acetonitrile (20 mL) was added 1,3-propane sultone (1.29 g, 10.6 mmol). The solution was stirred at reflux for 2.5 hours. The reaction mixture was cooled to room temperature. The solid was filtered and washed with acetonitrile (2×20 mL). The solid product was suspended in EtOH (75 mL). The suspension was stirred at reflux for 1 hours. The solid material was filtered, washed with acetone (1×25 mL) and dried in vacuo, affording the title compound (2.62 g, 89%). 1H NMR (D2O, 500 MHz) δ ppm 7.28 (m, 3H), 7.19 (m, 2H), 4.05 (m, 1H), 3.19 (dd, 1H, J=5.3 Hz, 14.2 Hz), 3.04 (m, 3H), 2.86 (t, 2H, J=5.8 Hz), 2.03 (m, 2H). 13C (D2O, 125 MHz) δ ppm 170.39, 133.73, 129.62, 129.26, 128.15, 61.57, 47.99, 45.57, 36.21, 21.45. [α]D=−20.7° (c=0.0038 in water), ES-MS 285 (M−1).

Workup

  1. temperatureat reflux for 2.5 hours
  2. filtrationThe solid was filtered
  3. washwashed with acetonitrile (2×20 mL)
  4. stirringThe suspension was stirred
  5. temperatureat reflux for 1 hours
  6. filtrationThe solid material was filtered
  7. washwashed with acetone (1×25 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-1459b54d87904f3f8a56cb1f8a285f68
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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