Water → HCID 3360956, compound

HRID 1616796Notes

Reaction equation

HRID 1616796 reaction equation
C(N(CC)CC)C.[CH2:8]([N:15]=[C:16]=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[CH3:19][O:20][C:21](=[O:31])[C@H:22]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH2:23].O>O1CCCC1>[CH2:8]([NH:15][C:16](=[O:17])[NH:23][CH:22]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:21]([O:20][CH3:19])=[O:31])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 76639Benzyl isocyanate

Product 1

HCID 3360956HCID 3360956, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (1.86 mmol, 0.26 ml) and benzyl isocyanate (1.86 mmol, 0.23 mL) were added at 0° C. to a solution of phenylalanine methylester hydrochloride (0.93 mmol, 0.2 g) in tetrahydrofuran, and the mixture was stirred over a period of 12 h. The reaction was poured into water (30 mL) and extracted with ethyl acetate (5×30 mL). The organic layers were washed with saturated sodium chloride solution (3×30 mL), dried with anhydrous sodium sulfate and concentrated. The residue was purified by chromatographic column on silica gel eluting with ethyl acetate/n-hexane 1/2 to afford the pure compound as a colorless oil, 95% yield; 1H NMR (CDCl3, 400 MHz, δ; ppm) δ 2.91-2.92 (dd, 1H, PhCHHCHCOO), 2.96-2.97 (dd, 1H, PhCHHCHCOO), 3.56 (s, 3H, COOCH3), 4.70-4.71 (m, 1H, PhCHHCHCOO), 4.17-4.19 (dd, 1H, PhCHHNHCONH), 4.22-4.24 (dd, 1H, PhCHHNHCONH), 5.46 (bs, 2H, NHCONH), 7.03-7.04 (2H, aromatic protons), 7.17-7.25 (m, 8H, aromatic protons); 13C NMR (CDCl3, 400 MHz, δ; ppm) δ 36.3, 44.4, 51.9, 57.3, 125.9, 126.7, 126.9 (2C), 127.7 (2C), 128.5 (2C), 128.6 (2C), 136.6, 137.9, 157.9, 171.5; MS (ESI) m/z: 312.14 [M]+.

Workup

  1. extractionextracted with ethyl acetate (5×30 mL)
  2. washThe organic layers were washed with saturated sodium chloride solution (3×30 mL)
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatographic column on silica gel eluting with ethyl acetate/n-hexane 1/2

Sources & evidence

ORD record
ord-c8900171a24544d4be35e274ddb0e906
Source dataset
uspto-grants-2014_07
Patent number
US08765820B2

Reaction notes

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