Benzylamine → HCID 19029179, compound

HRID 2256018Notes

Reaction equation

HRID 2256018 reaction equation
CN1CCOCC1.[C:8]([NH:11][CH:12]([CH2:16][CH:17]=[CH2:18])[C:13]([OH:15])=O)(=[O:10])[CH3:9].C(OC(Cl)=O)C(C)C.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[CH2:27]([NH:34][C:13](=[O:15])[CH:12]([NH:11][C:8](=[O:10])[CH3:9])[CH2:16][CH:17]=[CH2:18])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 321142N-ACETYL-DL-ALLYLGLYCINE

Product 1

HCID 19029179HCID 19029179, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Methylmorpholine (0.55 g, 5.40 mmol) was added to a cooled (-10° to -15° C.) THF solution (60 mL) of 2-acetamido-4-pentenoic acid (0.81 g, 5.18 mmol), and then isobutylchloroformate (0.75 g. 5.70 mmol) was added leading to the precipitation of a white solid. After 2 min, a solution of benzylamine (0.61 g, 5.70 mmol) in THF (10 mL) was slowly added at -10° to -15° C. The reaction was allowed to warm (5 min) at room temperature and the insoluble salts were removed by filteration, and the filtrate was evaporated to dryness. The residue was triturated with EtOAc (10 mL), and the remaining white solid was filtered to give 0.81 g (64%) of the desired product: mp 118°-120° C. (recrystallized from ethyl acetate/cyclohexane); Rf 0.36 (4% MeOH/CHCl3); IR (KBr) 3200 (br), 3040, 2900, 1650 (br), 1540 (br), 1350, 750, 700 cm-1 ; 1H NMR (DMSO-d6) δ 1.83 (s, C(O)CH3), 2.22-2.49 (m, CH2CH=CH2), 4.26 (d, J=5.3 Hz, CH2Ph), 4.25-4.33 (m, CH), 4.99-5.09 (m, CH2CH=CH2), 5.65-5.77 (m, CH2CH=CH2), 7.21-7.29 (m, 5 PhH), 8.05 (d, J=7.6 Hz, NH), 8.46 (br s, NH); 13C NMR (DMSO-d6) 22.41 (C(O)CH3), 36.24 (CH2CH=CH2), 41.91 (CH2Ph), 52.20 (CH), 117.15 (CH2CH=CH2), 126.54 (C4'), 126.99 (2C2' or 2C3'), 128.04 (2C2' or 2C3'), 139.25 (C1'), 134.25 (CH2CH=CH2), 169.02 (C(O)CH3), 170.96 (C(O)NH) ppm; mass spectrum, m/e (relative intensity) 246 (M+, 4), 205 (4), 163 (15), 140 (8), 106 (33), 91 (77), 70 (100).

Workup

  1. customleading to the precipitation of a white solid
  2. customthe insoluble salts were removed by filteration
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was triturated with EtOAc (10 mL)
  5. filtrationthe remaining white solid was filtered

Sources & evidence

ORD record
ord-c343d1e6f0a04778baf17f487d400805
Source dataset
uspto-grants-1997_08
Patent number
US05654301

Reaction notes

Loading…