Triethylamine → HCID 19003146, compound

HRID 2259290Notes

Reaction equation

HRID 2259290 reaction equation
Cl.[NH2:2][CH:3]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:4]([O:6][CH2:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=1)=[O:5].C(N(CC)CC)C.[CH3:33][N:34]=[C:35]=[O:36]>O1CCCC1>[CH3:33][NH:34][C:35](=[O:36])[NH:2][CH:3]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:4]([O:6][CH2:7][C:8]1[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=1)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 19003122HCID 19003122, compound

Product 1

HCID 19003146HCID 19003146, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-Dimethylbenzyl 2-amino-3-(3-indolyl)propionate hydrochloride (1.0 g) was suspended in tetrahydrofuran (10 ml). Triethylamine (0.38 ml) was added and the solution was stirred at room temperature for 15 minutes. Methyl isocyanate (0.19 ml) was added and the solution was stirred for 1 hour. The tetrahydrofuran was removed in vacuo and the residue was taken up in ethyl acetate. The organic phase was washed with dilute hydrochloric acid, water and sodium bicarbonate solution. The organic extract was dried (Na2SO4) and evaporated. The residual solid was recrystallised from ethyl acetate/petroleum ether to yield the title compound, (1.17 g), m.p. 66°-68° C. 1H NMR (360 MHz, CDCl3) δ7.99 (1H, s), 7.52 (1H, d, J=8 Hz), 7.30 (1H, d, J=8 Hz), 7.16 (1H, t, J=8 Hz), 7.08 (1H, t, J=8 Hz), 6.96 (1H, s), 6.88 (2H, s), 6.76 (1H, s), 5.01 (2H, s), 4.83 (1H, m), 3.26 (2H, d, J=5 Hz), 2.65 (3H, s), 2.30 (6H, s). Found: C, 68.64; H, 6.36; N, 10.86. C22H25O3N3. 0.3(H2O) requires C, 68.57; H, 6.66; N, 10.90.

Workup

  1. stirringthe solution was stirred for 1 hour
  2. customThe tetrahydrofuran was removed in vacuo
  3. washThe organic phase was washed with dilute hydrochloric acid, water and sodium bicarbonate solution
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. customevaporated
  7. customThe residual solid was recrystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-67a0627c93224f94b4bde1531a68602d
Source dataset
uspto-grants-1995_12
Patent number
US05472978

Reaction notes

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