Triphenylphosphine → HCID 69317624, compound

HRID 1393518Notes

Reaction equation

HRID 1393518 reaction equation
C1(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][C@H:45]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:46]([NH2:48])=[O:47])(=[O:43])=[O:42])=[CH:37][CH:36]=1.[CH3:55][O:56][C:57](=[O:66])[C:58]1[CH:63]=[CH:62][C:61]([CH2:64]O)=[CH:60][CH:59]=1>O1CCCC1>[CH3:55][O:56][C:57](=[O:66])[C:58]1[CH:63]=[CH:62][C:61]([CH2:64][N:44]([C@@H:45]([C:46](=[O:47])[NH2:48])[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[S:41]([C:38]2[CH:39]=[CH:40][C:35]([Cl:34])=[CH:36][CH:37]=2)(=[O:42])=[O:43])=[CH:60][CH:59]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 81325Methyl 4-(hydroxymethyl)benzoateHCID 51536914HCID 51536914, compound

Product 1

HCID 69317624HCID 69317624, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of triphenylphosphine (48 mmg, 0.2 mmol) in 0.7 mL of tetrahydrofuran is added diisopropyl azodicarboxylate (0.04 mL, 0.2 mmol) and the reaction stirred for 30 min. To the reaction is added 0.4 mL of tetrahydrofuran, (R)-2-(4-chloro-benzenesulfonylamino)-2-phenyl-acetamide (32 mg, 0.2 mmol), and methyl-4-hydroxymethylbenzoate (73 mg, 0.2 mmol). The reaction is allowed to warm to room temperature 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) 49.9, 52.3, 64.4, 127.9, 129.0, 129.2, 129.4, 129.5, 130.1, 133.5, 139.7, 142.5, 167.0, 171.0. MS 473.1 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-614b8700f44d47e781cbd4b3b32e800e
Source dataset
uspto-grants-2008_03
Patent number
US07345095B2

Reaction notes

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