Acetic Acid → 3-(4-Benzyloxyphenyl)-2-diazo propionic acid methyl ester

HRID 1597441Notes

Reaction equation

HRID 1597441 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[NH2:5].[N:22](OCCC(C)C)=O.C(O)(=O)C>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[C:4](=[N+:5]=[N-:22])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8053Isoamyl NitriteHCID 6999558H-Tyr(Bzl)-OMe

Product 1

HCID 542667363-(4-Benzyloxyphenyl)-2-diazo propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2.5 g (8.77 mmol) O-benzyl tyrosine methyl ester, 1.03 g (8.77 mmol) isoamyl nitrite, and 1.57 g (26.2 mmol) glacial acetic acid in chloroform (65 mL) was stirred and refluxed 15 min and then cooled to RT. The solution was concentrated to an oily residue, dissolved in EtOAc (100 mL), and washed with 5% NaHCO3. The organics were then dried (MgSO4), filtered, and concentrated to an oily residue which was chromatographed on silica gel using Hexane/EtOAc (1:1) to yield the title compound. 1H NMR (CDCl3) δ 7.43-7.31 (m, 5H) 7.14 (d, 2H, J=8.7) 6.90 (m, 2H) 5.03 (s, 2H) 3.76 (s, 3H) 3.56 (s, 2H).

Workup

  1. temperaturerefluxed 15 min
  2. concentrationThe solution was concentrated to an oily residue
  3. dissolutiondissolved in EtOAc (100 mL)
  4. washwashed with 5% NaHCO3
  5. dry with materialThe organics were then dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to an oily residue which
  8. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-9119fde21ec645f2bf1fa288ec84a230
Source dataset
uspto-grants-2001_09
Patent number
US06294580B1

Reaction notes

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