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

HRID 660605

Reaction equation

HRID 660605 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 THF is added PPh3 (1.7 g, 6.5 mmol) and DEAD (2.97 mL, 6.5 mmol) and the mixture is stirred at RT overnight. The solvent is removed under reduced pressure and the residue is purified by flash chromatography eluting with hexanes/EtOAc (5:1 to 2:1) to give the title compound as a colorless liquid: 1H NMR (CDCl3) δ 11.42 (s, 1H), 7.29 (t, J=8.34 Hz, 1H), 6.57 (d, J=8.34 Hz, 1H), 6.37 (d, J=8.34 Hz, 1H), 4.63 (s, 1H), 3.99 (t, J=6.06 Hz, 2H), 3.93 (s, 3H), 3.22-3.17 (m, 2H), 1.88-1.81 (m, 2H), 1.74-1.67 (m, 2H), 1.43 (s, 9H); (M−1)−=338.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is purified by flash chromatography
  3. washeluting with hexanes/EtOAc (5:1 to 2:1)

Sources & evidence

ORD record
ord-3c414c6b6e24485bbfcf811e7f09c1e5
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Linked notes

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