Triphenylphosphine → HCID 67338768, compound

HRID 1921202Notes

Reaction equation

HRID 1921202 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[O:13]=[C:14]1[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[NH:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:49]1[CH2:54][CH2:53][CH:52](O)[CH2:51][CH2:50]1>C1COCC1>[O:13]=[C:14]1[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]1[CH:52]1[CH2:53][CH2:54][S:49][CH2:50][CH2:51]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 576296Tetrahydro-2H-thiopyran-4-olHCID 2756037tert-Butyl 2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate

Product 1

HCID 67338768HCID 67338768, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (446 mg, 2.56 mmol) was added to a solution of tert-butyl 2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate (J. Org. Chem., 1995, 60, 1565-1582) (500 mg, 2.13 mmol), triphenylphosphine (672 mg, 2.56 mmol), and tetrahydro-2H-thiopyran-4-ol (Chem. Comm., 2002, 10, 1070-1071) (303 mg, 2.56 mmol) in THF (10 mL). After 20 h, the reaction was concentrated in vacuo and the crude product purified by silica gel column chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 95:5, to give the title compound. MS: m/z=335 (M+1).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customthe crude product purified by silica gel column chromatography
  3. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-05f9d06a373d4e67a93c9f46ae1d50bd
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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