Triphenylphosphine → HCID 131729957, compound

HRID 2389512Notes

Reaction equation

HRID 2389512 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1OC)[C:6]([OH:8])=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)(C)C)=O)=O)(C)(C)C.[F:49][C:50]1[CH:67]=[CH:66][C:53]2[N:54]([CH2:58][C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[C:55]([SH:57])=[N:56][C:52]=2[CH:51]=1>C1COCC1>[C:62]([O:61][C:59](=[O:60])[CH2:58][N:54]1[C:53]2[CH:66]=[CH:67][C:50]([F:49])=[CH:51][C:52]=2[N:56]=[C:55]1[S:57][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:5]([C:6]([OH:8])=[O:7])[CH:4]=1)([CH3:65])([CH3:63])[CH3:64]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 53896293HCID 53896293, compoundHCID 178451225HCID 178451225, compound2×

Product 1

HCID 131729957HCID 131729957, compoundYield 181.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hydroxymethyl-4-methoxy-benzoic acid (Starting material H-00e, 910 mg, 5 mmol) in dry THF (50 ml) cooled to 0° C. under inert atmosphere are added successively triphenylphosphine (1782 mg, 6 mmol, 1.2 eq.) and di-tert-butyl-azodicarboxylate (1381 mg, 6 mmol, 1.2 eq). The initially deep yellow colour disappears after 10 min. Then tert-butyl (5-fluoro-2-mercapto-benzoimidazol-1-yl)-acetate (Intermediate 3-III, 1270 mg, 0.9 mmol, 0.9 eq.) is added. The reaction mixture is allowed to warm up to rt and stirred at this temperature for 1 h. Evaporation of the solvent in vacuo and purification by flash-chromatography on silica gel (AcOEt/heptane/AcOH, 10:90:1), provides the title compound (680 mg) in 30% as beige solid:

Workup

  1. customEvaporation of the solvent
  2. customin vacuo and purification by flash-chromatography on silica gel (AcOEt/heptane/AcOH, 10:90:1)

Sources & evidence

ORD record
ord-d67c6a22e3224e14964ff968904eab32
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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