Potassium Carbonate → HCID 131712164, compound

HRID 894350Notes

Reaction equation

HRID 894350 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C(=O)([O-])[O-].[K+].[K+].[C:21]([N:31]1[CH2:49][CH2:48][CH2:47][C@H:32]1[C:33]([NH:35][C:36]([C:44](O)=[O:45])=[CH:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:34])([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][C:44](=[O:45])[C:36](=[CH:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[NH:35][C:33](=[O:34])[C@@H:32]1[CH2:47][CH2:48][CH2:49][N:31]1[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 131712165HCID 131712165, compound

Product 1

HCID 131712164HCID 131712164, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.759 g (0.0036 mole) of L-phenylalanine methyl ester hydrochloride and 40 ml of ethyl acetate was cooled in an ice-bath and 15 ml of cold 505 potassium carbonate solution was added. The mixture was equilibrated, and the ethyl acetate layer was separated and dried over anhydrous Na2SO4 at 0°. To the solution 1.129 g (0.003 mole) of the azlactone of N-carbobenzoxy-L-prolyl-dehydrophenylalanine was added. The reaction mixture was then refluxed for 8 hours, cooled and washed with N-hydrochloric acid, saturated sodium bicarbonate solution, saturated sodium chloride solution and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo and the residual crystals were recrystallized from ethyl acetate/petroleum ether giving 1.473 g (88%) of N-carbobenzoxy-L-prolyl-dehydrophenylalanyl-L-phenylalanine methyl ester, mp 161°-163.5°, RfA 0.95, [α]D26 =-94.3° (c, 1% in EtOH); ir (CHCl3) 1735 (C=) 1690-1670 (C=O), 1630 cm-1 (C=C); NMR (CDCl3) δ1.5-2.4 (m, 4H, Pro ring), 3.0-3.33 (m, 2H, --CHCH2Ph), 3.33-3.57 (m, 2H, Pro ring) 3.63 (s, 3H, --COOCH3), 4.17-4.53 (m, 1H, --CH-CH2Ph), 4.67-5.0 (m, 1H, Pro ring), 5.02 (br.s., 2H>NOCOCH2Ph) 6.83-7.47 (m, 11H, ArH and PhCH=C<), 7.9-8.1 ppm (b, 2 H, NH, exchange by D2O).

Workup

  1. temperaturewas cooled in an ice-bath
  2. customthe ethyl acetate layer was separated
  3. dry with materialdried over anhydrous Na2SO4 at 0°
  4. temperatureThe reaction mixture was then refluxed for 8 hours
  5. temperaturecooled
  6. washwashed with N-hydrochloric acid, saturated sodium bicarbonate solution, saturated sodium chloride solution
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe solvent was evaporated in vacuo
  9. customthe residual crystals were recrystallized from ethyl acetate/petroleum ether giving 1.473 g (88%) of N-carbobenzoxy-L-prolyl-dehydrophenylalanyl-L-phenylalanine methyl ester, mp 161°-163.5°, RfA 0.95, [α]D26 =-94.3° (c, 1% in EtOH)

Sources & evidence

ORD record
ord-3d87f89cbc7b4626b9319792f53dd237
Source dataset
uspto-grants-1981_08
Patent number
US04283328

Reaction notes

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