Allylamine → HCID 131718648, compound

HRID 1742747Notes

Reaction equation

HRID 1742747 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.O[N:25]1[C:29]2C=CC=[CH:33][C:28]=2N=N1.Cl.CN(C)CCCC(N=C=N)C.C(N)C=C>C(Cl)Cl>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[CH2:29]([NH-:25])[CH:28]=[CH2:33]

Participants

6

Reactant 4

HCID 7853AllylamineHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 27960291-Hydroxybenzotriazole hydrateHCID 219829211-(3-Dimethylaminopropyl)ethylcarbodiimide hydrochloride

Product 1

HCID 131718648HCID 131718648, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, Cbz-Phe-OH (1.00 g, 3.35 mmol) was dissolved in 10 mL of anhydrous methylene chloride containing 1-hydroxybenzotriazole monohydrate (0.57 g, 3.69 mmol) and 1-(3-dimethylaminopropyl)-ethylcarbodiimide hydrochloride (0.71 g, 3.69 mmol) and stirred at ice bath temperature for 1.5 hour. Allylamine (0.19 g, 3.35 mmol) was added and the solution was stirred at 0° C. for 5 hours and then allowed to warm to ambient temperature overnight. The solvent was evaporated, and the residue was dissolved in ethyl acetate and washed with saturated aqueous KHSO4, water, saturated aqueous sodium bicarbonate, water, and brine, prior to drying and evaporation. Recrystallization from ethyl acetate/hexane afforded 0.56 g (50% yield) of the title compound as a white solid product; 1H NMR (CDCl3) δ3.03 (dd, J=15 and 7.5 Hz, 1H), 3.14 (dd, J=15 and 7.5 Hz, 1H), 3.76-3.82 (m, 2H), 4.33-4.42 (m, 1H), 4.96-5.08 (m, 2H), 5.10 (s, 2H), 5.33 (br s, 1H), 5.59-5.74 (m, 2H), 7.15-7.40 (m, 10H). MS (DCI) m/e 356 (M+NH4)+, 339 (M+H)+.

Workup

  1. stirringthe solution was stirred at 0° C. for 5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous KHSO4, water, saturated aqueous sodium bicarbonate, water, and brine
  5. customto drying
  6. customevaporation
  7. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-246babec8662452598f166eb8d6a6e18
Source dataset
uspto-grants-1994_08
Patent number
US05340802

Reaction notes

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