Triethylamine → HCID 53722037, compound

HRID 1728452Notes

Reaction equation

HRID 1728452 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](Cl)=[O:12])=[CH:5][CH:4]=1.Cl.[CH3:15][O:16][C:17](=[O:27])[C@H:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH2:19].C(N(CC)CC)C.CCOC(C)=O>ClCCl>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([NH:19][C@H:18]([C:17]([O:16][CH3:15])=[O:27])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 19018249HCID 19018249, compound

Product 1

HCID 53722037HCID 53722037, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 1.6 g (6.2 mmol) of 3-[4-(chloromethyl)phenyl]propionyl chloride and 1.3 g (6.2 mmol) of phenylalanine methyl ester hydrochloride salt in 6 ml of dichloromethane was added 1.4 g (14 mmol) of triethylamine. The reaction mixture was stirred at 0° C. for 0.5 hour, poured into EtOAc and washed with water. The EtOAc layer was dried over Na2SO4, filtered and evaporated to afford an oil. This oil was flash chromatographed (40% EtOAc/hexanes) to give 0.8 g of product; m.p. 89°-90° C.

Workup

  1. washwashed with water
  2. dry with materialThe EtOAc layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customto afford an oil
  6. customchromatographed (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-80f82b71842848c59800a89587149eac
Source dataset
uspto-grants-1994_07
Patent number
US05326905

Reaction notes

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