Propane sultone → 3-{[(1S)-1-carbamoyl-2-phenylethyl]amino}-1-propanesulfonic acid

HRID 239777

Reaction equation

HRID 239777 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 445694Phenylalanine amide

Product 1

HCID 160361773-{[(1S)-1-carbamoyl-2-phenylethyl]amino}-1-propanesulfonic acidYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of L-Phenylalaninamide (3.93 g, 23.9 mmol) in acetonitrile (25 mL) was added 1,3-propane sultone (2.70 g, 21.8 mmol). The solution was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid was filtered and washed with acetonitrile (2×25 mL). The solid product was suspended in EtOH (100 mL). The suspension was stirred at reflux for 1 hour. The solid material was filtered and dried in vacuo, affording the title compound (5.18 g, 83%). 1H NMR (D2O, 500 MHz) δ ppm 7.24 (m, 3H), 7.16 (m, 2H), 4.02 (m, 1H), 3.15 (m, 1H), 3.01 (m, 3H), 2.83 (m, 2H), 2.02 (m, 2H), 1.98 (m, 2H). 13C (D2O, 125 MHz) δ ppm 170.48, 133.72, 129.58, 129.21, 128.11, 61.55, 47.95, 45.52, 36.21, 21.44. [α]D=+23.1° (c=0.0021 in water), ES-MS 285 (M−1).

Workup

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

Sources & evidence

ORD record
ord-7f8de3f293324474aa3c0d9b5d12d588
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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