1,2-Dichloroethane → HCID 7033973, compound

HRID 342876Notes

Reaction equation

HRID 342876 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC1C(O)=C(F)C(F)=C(F)C=1F.C(Cl)CCl.[NH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>ClCCl>[C:40]1([NH:39][C:20](=[O:22])[C@H:12]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 13041PentafluorophenolHCID 70878Benzyloxycarbonyl-L-phenylalanine

Product 1

HCID 7033973HCID 7033973, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Nα -Benzyloxycarbonyl-L-phenylalanine (4.95 g, 16.5 mmol) was dissolved in dichloromethane (70 ml) and the solution was cooled to 0° C. and stirred during the addition of pentafluorophenol (3.35 g, 18.2 mmol), followed by EDC (3.49 g, 18.2 mmol). The mixture was allowed to warm to room temperature, stirred for a further 1 hour then cooled back to 0° C. Aniline (3.85 g, 41.4 mmol) was added dropwise and the mixture was warmed to room temperature then stirred overnight. The solution was washed twice with 1M sodium carbonate, twice with 1M hydrochloric acid and finally with brine before drying over anhydrous magnesium sulphate. The solution was filtered and evaporated to a white solid which was recrystallised from ethyl acetate-hexane. Yield: 2.57 g (41%). 1H-NMR; δ (CDCl3), 7.87 (1H, brs), 7.43-7.03 (15H, br m), 5.62 (1H, m), 5.08 (2H, s), 4.59 (1H, s) and 3.15 (2H, s).

Workup

  1. temperatureto warm to room temperature
  2. temperaturethen cooled back to 0° C
  3. temperaturethe mixture was warmed to room temperature
  4. stirringthen stirred overnight
  5. washThe solution was washed twice with 1M sodium carbonate, twice with 1M hydrochloric acid and finally with brine
  6. dry with materialbefore drying over anhydrous magnesium sulphate
  7. filtrationThe solution was filtered
  8. customevaporated to a white solid which
  9. customwas recrystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e30f50bb72ae4626b97ddf254cb972c7
Source dataset
uspto-grants-1999_01
Patent number
US05859253

Reaction notes

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