Isopropyl isocyanate → 3-[4-Hydroxy-2-(3-isopropyl-ureidomethyl)-phenyl]-propionic acid tert-butyl ester

HRID 1181043Notes

Reaction equation

HRID 1181043 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][NH2:17])([CH3:4])([CH3:3])[CH3:2].[CH:19]([N:22]=[C:23]=[O:24])([CH3:21])[CH3:20]>C(Cl)Cl.O>[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][NH:17][C:23]([NH:22][CH:19]([CH3:21])[CH3:20])=[O:24])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 61277Isopropyl isocyanateHCID 17984622Tert-butyl-3-[2-(aminomethyl)-4-hydroxyphenyl]propanoate

Product 1

HCID 589790703-[4-Hydroxy-2-(3-isopropyl-ureidomethyl)-phenyl]-propionic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A slurry of 3-(2-aminomethyl-4-hydroxy-phenyl)-propionic acid tert-butyl ester (2.24 g, 8.91 mmol) in CH2Cl2 (30 mL) was treated with isopropyl isocyanate (1.1 mL, 11 mmol). The reaction mixture was diluted with water, the CH2Cl2 was removed under reduced pressure, and the aqueous layer was extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated to the title compound as a white solid (2.6 g, 87%). MS (ES+) m/z 337 [M+H]+.

Workup

  1. customthe CH2Cl2 was removed under reduced pressure
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated to the title compound as a white solid (2.6 g, 87%)

Sources & evidence

ORD record
ord-3ea142f1a1bc42e09d9379c18c8259f6
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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