Triphenylphosphine → HCID 69774812, compound

HRID 2120649Notes

Reaction equation

HRID 2120649 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:22][C:23](=[O:47])[CH2:24][C@@H:25]([C:39]1[CH:40]=[N:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=1)[NH:26][S:27]([C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH3:21].N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1COCC1.CO>[CH2:20]([O:22][C:23](=[O:47])[CH2:24][C@@H:25]([C:39]1[CH:40]=[N:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=1)[N:26]([CH3:1])[S:27]([C:30]1[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=1)(=[O:28])=[O:29])[CH3:21]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 69666587HCID 69666587, compound

Product 1

HCID 69774812HCID 69774812, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Triphenylphosphine (3.9 g, 15 mmol) was added to a solution of sulfonamide 1-6 (4.5 g, 10 mmol) in THF (30 mL). To this solution was added a solution of diethyl azodicarboxylate (2.4 mL, 15 mmol) in THF/MeOH (10 mL/2.02 mL). A vigorous exotherm occurred and the reaction was stirred overnight at room temperature. The dark mixture was concentrated. The dark oily residue was purified by flash chromatography (40% EtOAc/hexanes) to give the desired product 1-7.

Workup

  1. concentrationThe dark mixture was concentrated
  2. customThe dark oily residue was purified by flash chromatography (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6b047af4966c4025982b058756240912
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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