Triphenylphosphine → Methyl 2-{4-[(tert-butoxycarbonyl)amino]butoxy}-6-hydroxybenzoate

HRID 889274

Reaction equation

HRID 889274 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24]O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:7][O:6][C:4](=[O:5])[C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[CH:9][C:8]=1[O:12][CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 519869Methyl 2,6-dihydroxybenzoateHCID 545141tert-Butyl N-(4-hydroxybutyl)carbamateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 10980693Methyl 2-{4-[(tert-butoxycarbonyl)amino]butoxy}-6-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2,6-dihydroxybenzoate (1.0 g, 5.95 mmol) and 4-(Boc-amino)-1-butanol (1.1 mL, 5.95 mmol) in 60 mL of THF is added PPh3 (1.7 g, 6.5 mmol) and DEAD (2.97 mL, 6.5 mmol). The solution is stirred at RT for 18 h then the solvent is removed under reduced pressure. The residue is purified by flash chromatography using a gradient of hexane/EtOAc (5:1 to 2:1) to give the product as a colorless liquid.

Workup

  1. customthe solvent is removed under reduced pressure
  2. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-cd05ecbb491847059ab2dc8b69449f5a
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Linked notes

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