Acetic Acid → Ethyl 2-(N,N-diethylamino)-3-(4-hydroxyphenyl)propionate

HRID 1860105Notes

Reaction equation

HRID 1860105 reaction equation
[C:1](O)(=O)[CH3:2].[CH:5](=O)[CH3:6].Cl.[CH2:9]([O:11][C:12](=[O:23])[CH:13]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[NH2:14])[CH3:10].C([BH3-])#N.[Na+]>CO>[CH2:5]([N:14]([CH:13]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1)[C:12]([O:11][CH2:9][CH3:10])=[O:23])[CH2:1][CH3:2])[CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 61327DL-Tyrosine ethyl ester hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18625709Ethyl 2-(N,N-diethylamino)-3-(4-hydroxyphenyl)propionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid (0.3 ml) and acetaldehyde (0.5 ml) were added to a solution of DL-tyrosine ethyl ester hydrochloride (491 mg) in methanol (5 ml). To the mixture sodium cyanoborohydride (126 mg) was added and the mixture was stirred at ambient temperature for 2 hours. At the end of this time the reaction mixture was concentrated. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and washed with aqueous sodium hydrogencarbonate solution and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on a silica gel column using methanol/dichloromethane=1/20 as the eluant to afford the desired compound (420 mg) as a syrup.

Workup

  1. concentrationAt the end of this time the reaction mixture was concentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed with aqueous sodium hydrogencarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-a40dc8321b724fc1ac3333a9b5dbfdec
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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