Benzyl Alcohol → HCID 11589143, compound

HRID 901211Notes

Reaction equation

HRID 901211 reaction equation
[O:1]=[C:2]1[CH:11]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[NH:3]1.[CH2:23](O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.O1CCOCC1>[CH2:23]([N:3]1[C:4]2[C:9](=[CH:8][N:7]=[CH:6][CH:5]=2)[CH2:10][CH:11]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:2]1=[O:1])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58670147HCID 58670147, compound

Product 1

HCID 11589143HCID 11589143, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1E (297 mg, 1 mmol) in THF (8 mL) and 1,4-dioxane (6 mL) was added benzyl alcohol (103 μL, 1 mmol) and triphenylphosphine (393.5 mg, 1.5 mmol), followed by diethyl azodicarboxylate (0.24 mL, 1.5 mmol). The reaction mixture was stirred at RT for 10 min. After this time, no starting material was detected by LC-MS. The reaction was concentrated. The residue was purified by silica gel (40 g) column chromatography eluting with a gradient of methonal (0-5%) in EtOAc to give the title compound as a white solid (260 mg, 67%). LC/MS (method A): retention time=2.50 min, (M+H)+=388.

Workup

  1. concentrationThe reaction was concentrated
  2. customThe residue was purified by silica gel (40 g) column chromatography
  3. washeluting with a gradient of methonal (0-5%) in EtOAc

Sources & evidence

ORD record
ord-cd5f828ab38d4fa99145bf4e5c3cb325
Source dataset
uspto-grants-2008_04
Patent number
US07361766B2

Reaction notes

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