Triphenylphosphine → HCID 22225460, compound

HRID 2223234Notes

Reaction equation

HRID 2223234 reaction equation
[CH2:1]([O:8][NH:9][C:10](=O)[CH:11]([CH2:17][OH:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([O:8][N:9]1[CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:17]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22225487HCID 22225487, compound

Product 1

HCID 22225460HCID 22225460, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-hydroxymethyl-heptanoic acid benzyloxyamide (5.36 g, 20.23 mmol) and triphenylphosphine (5.31 g, 20.23 mmol) in THF (200 mL) at 0° C. was added dropwise diethyl azodicarboxylate (3.3 mL, 20.23 mmol). The reaction was stirred at room temperature overnight. The reaction was then quenched by adding water (200 mL). The aqueous layer was extracted with EtOAc (200 mL×2). The combined organic layer was washed with brine, and dried over MgSO4. After removing the solvent under vacuum, the residue was purified by flash column chromatography (hexane:EtOAc 5/1) to provide the title compound (4.68 g, 94%). 1H NMR (400 MHz, CHCl3) δ 7.35–7.25 (m, 5H), 4.87 (s, 2H), 3.28 (t, J=4.85 Hz, 1H), 2.84 (q, J=2.35 Hz, 1H), 2.77 (m, 1H), 1.62 (m, 1H), 1.36 (m, 1H), 1.25 –1.16 (m, 6H), 0.88 (t, J=6.9 Hz, 3H). MH+ 248.

Workup

  1. customThe reaction was then quenched
  2. additionby adding water (200 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (200 mL×2)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customAfter removing the solvent under vacuum
  7. customthe residue was purified by flash column chromatography (hexane:EtOAc 5/1)

Sources & evidence

ORD record
ord-468d767bb29f42c3bb2cc02ebfb172d0
Source dataset
uspto-grants-2008_05
Patent number
US07375120B2

Reaction notes

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