Methylparaben → HCID 67777625, compound

HRID 1026212Notes

Reaction equation

HRID 1026212 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.O[CH2:13][C@@H:14]([NH:16][C:17](=[O:23])OC(C)(C)C)[CH3:15].[C:24]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1>[C:17]([NH:16][C@@H:14]([CH3:15])[CH2:13][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)(=[O:23])[CH3:24]

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 67777625HCID 67777625, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-hydroxybenzoate (4.77 g), tert-butyl [(1S)-2-hydroxy-1-methylethyl]carbamate (5.00 g) and triphenylphosphine (11.2 g) in THF (70 mL) was added dropwise a toluene solution (2.2 M, 20 mL) of diethyl azodicarboxylate, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate). Using the obtained residue, and in the same manner as in Example 1, step D, the title compound (3.80 g) was obtained.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-dbcd46f6e3754f1aae6328cdf7e6016a
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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