Methylparaben → HCID 11213925, compound

HRID 1373739Notes

Reaction equation

HRID 1373739 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([S:41]([NH:44][CH:45]([CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:46]([NH2:48])=[O:47])(=[O:43])=[O:42])=[CH:37][CH:36]=1.[CH3:56][O:57][C:58](=[O:66])[C:59]1[CH:64]=[CH:63][C:62](O)=[CH:61][CH:60]=1>O1CCCC1>[CH3:56][O:57][C:58](=[O:66])[C:59]1[CH:64]=[CH:63][C:62]([CH2:1][N:44]([CH:45]([C:46](=[O:47])[NH2:48])[CH2:49][C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[S:41]([C:38]2[CH:39]=[CH:40][C:35]([Cl:34])=[CH:36][CH:37]=2)(=[O:42])=[O:43])=[CH:61][CH:60]=1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 3380937HCID 3380937, compound

Product 1

HCID 11213925HCID 11213925, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of triphenylphosphine (110 mmg, 0.4 mmol) in 0.7 mL of tetrahydrofuran is added diisopropyl azodicarboxylate (0.08 mL, 0.4 mmol) and the reaction stirred for 30 min. To the reaction is added 0.4 mL of tetrahydrofuran, (2-(4-chloro-benzenesulfonylamino)-3-phenyl-propionamide (75 mg, 0.2 mmol), and methyl-4-hydroxybenzoate (73 mg, 0.4 mmol). The reaction is allowed to warm to room temperature (rt) and stirred overnight. The solvent is removed and the resultant residue purified by silica gel chromatography to provide the title compound. C13 NMR (100 MHz, CDCl3) 35.5, 48.7, 52.4, 61.4, 127.1, 128.8, 128.9, 129.0, 129.3, 129.6, 129.9, 136.8, 138.1, 139.8, 141.7, 166.9, 171.0. MS 487.1 m/z (M+1).

Workup

  1. stirringstirred overnight
  2. customThe solvent is removed
  3. customthe resultant residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-a7e71602c19446fb9aebc44135ebee44
Source dataset
uspto-grants-2007_01
Patent number
US07163942B2

Reaction notes

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