Benzylamine → HCID 19029222, compound

HRID 2256017Notes

Reaction equation

HRID 2256017 reaction equation
CN1CCOCC1.[C:8]([NH:11][CH:12]([CH:16]=[CH2:17])[C:13]([OH:15])=O)(=[O:10])[CH3:9].C(OC(Cl)=O)C(C)C.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[C:8]([NH:11][CH:12]([CH:16]=[CH2:17])[C:13]([NH:33][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:15])(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 13246942HCID 13246942, compound

Product 1

HCID 19029222HCID 19029222, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Methylmorpholine (0.71 g, 6.99 mmol) was added to a suspension of 2-acetamido-2-vinylacetic acid (1.00 g, 6.99 mmol) in THF (325 mL), and the mixture was stirred at room temperature (30 min). The reaction was cooled to -10° to -15° C. and then isobutylchloroformate (1.24 g, 9.08 mmol) was then added dropwise. After stirring (10 min), a solution of benzylamine (0.75 g, 6.99 mmol) in THF (25 mL) was added (15 min). The reaction mixture was allowed to warm to 0° C. The insoluble material was filtered. The filtrate was concentrated in vacuo, and the residue was purified by flash column chromatography on SiO2 gel using 3% MeOH/CHCl3 as the eluant to give 1.00 g (62%) of the desired product: mp 136°-138° C. (recrystallized from EtOAc); Rf 0.24 (3% MeOH/CHCl3); 1H NMR (DMSO-d6) δ 1.88 (s, C(O)CH3), 4.27 (d, J=5.6 Hz, CH2), 4.89-4.94 (dd, J=6.4, 7.8 Hz, α-CH), 5.13-5.30 (m, --CH=CH2), 5.81-5.93 (m, --CH=CH2), 7.20-7.33 (m, 5 PhH), 8.27 (c, J=7.8 Hz, NH), 8.58 (t, J=5.6 Hz, NH); 13C NMR (DMSO-d6) 22.47 (C(O)CH3), 42.05 (CH2), 55.24 (α-CH), 116.44 (CH=CH2), 126.74 (C4'), 127.05 (2C2' or 2C3'), 128.24 (2C2' or 2C3'), 134.76 (CH=CH2), 139.25 (C1'), 168.78 (C(O)CH3), 168.99 (C(O)NH) ppm.

Workup

  1. temperatureThe reaction was cooled to -10° to -15° C.
  2. stirringAfter stirring (10 min)
  3. temperatureto warm to 0° C
  4. filtrationThe insoluble material was filtered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by flash column chromatography on SiO2 gel

Sources & evidence

ORD record
ord-9e0d841520c449d987047048e56fe2d1
Source dataset
uspto-grants-1997_08
Patent number
US05654301

Reaction notes

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