DL-Tyrosine → HCID 21023684, compound

HRID 1743116Notes

Reaction equation

HRID 1743116 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].Cl[C:15]1[N:20]=[C:19](Cl)[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][N:16]=1.C([N:28]([CH2:32][CH3:33])[CH:29]([CH3:31])C)(C)C.[CH2:34](NCC)C.[CH2:39]1[CH2:43]OC[CH2:40]1>C(OCC)C>[CH2:32]([N:28]([CH2:29][CH3:31])[C:15]1[N:20]=[C:19]([NH:1][CH:2]([CH2:6][C:7]2[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=2)[C:3]([O:5][C:39]([CH3:40])([CH3:43])[CH3:34])=[O:4])[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][N:16]=1)[CH3:33]

Participants

7

Reactant 5

HCID 1153DL-TyrosineHCID 8021DiethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 21023684HCID 21023684, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 2-amino-3-(4-hydroxyphenyl)propionic acid, (30.6 g, 0.129 mol) in THF (250 mL) at −10° C. was added 2,4-Dichloro-5-nitropyrimidine (25 g, 0.129 mol), keeping the temperature below 5° C. during the addition. Once the addition was complete, N,N-diisopropylethylamine (33.7 mL, 0.194 mol) was added dropwise. After stirring for 1 h at −10° C., diethylamine (66.73 mL, 0.645 mol) was added slowly, and then the reaction mixture was warmed to room temperature overnight. The reaction mixture was diluted with diethyl ether (500 mL), and the organic layer was washed with 0.2 N citric acid (3×150 mL), water (1×150 mL), and 10% K2CO3 (3×150 mL). The organic phase was dried (Na2SO4), filtered, and concentrated in vacuo to yield a yellow residue. The residue was purified by flash chromatography (20% EtOAc/hexanes on silica gel) to yield 37.39 g (67%) the title compound as a yellow foam. Rf=0.21 (25% EtOAc/hexanes on silica gel).

Workup

  1. customthe temperature below 5° C.
  2. additionduring the addition
  3. additionOnce the addition
  4. temperaturethe reaction mixture was warmed to room temperature overnight
  5. washthe organic layer was washed with 0.2 N citric acid (3×150 mL), water (1×150 mL), and 10% K2CO3 (3×150 mL)
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield a yellow residue
  10. customThe residue was purified by flash chromatography (20% EtOAc/hexanes on silica gel)

Sources & evidence

ORD record
ord-eec8c67049a848fdbd5f024d833b0a4d
Source dataset
uspto-grants-2006_03
Patent number
US07008949B2

Reaction notes

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