Triphenylphosphine → Methyl 3-(3-{[(benzyloxy)carbonyl]amino}propoxy)benzoate

HRID 1713855Notes

Reaction equation

HRID 1713855 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].O[CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:19]([O:18][C:17]([NH:16][CH2:15][CH2:14][CH2:13][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 88068Methyl 3-HydroxybenzoateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 562256Benzyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 59464335Methyl 3-(3-{[(benzyloxy)carbonyl]amino}propoxy)benzoateYield 38.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of methyl 3-hydroxybenzoate (609 mg, 4 mmol), benzyl N-(3-hydroxypropyl)carbamate (754 mg, 3.6 mmol) and polymer supported triphenylphosphine (PS—PPh3) (4 g, 12 mmol) in THF (40 mL) was stirred and diethyl azodicarboxylate (948 mg, 5.44 mmol) was added as a solution in THF (4 mL). The mixture was stirred for 16 h then was filtered and washed with DCM and concentrated by evaporation. The residue was purified by chromatography eluting with DCM to give the title compound (481 mg, 35%) as an oil; 1H NMR δ 1.85-1.92 (2H, m), 3.19 (2H, q), 3.86 (3H, s), 4.05 (2H, t), 5.02 (2H, s), 7.20-7.22 (1H, m), 7.29-7.38 (5H, m), 7.42-7.45 (2H, m), 7.53-7.56 (1H, m).

Workup

  1. stirringThe mixture was stirred for 16 h
  2. filtrationthen was filtered
  3. washwashed with DCM
  4. concentrationconcentrated by evaporation
  5. customThe residue was purified by chromatography
  6. washeluting with DCM

Sources & evidence

ORD record
ord-b7c2e756bfa34b4bbd372065cd74adff
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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