Triphenylphosphine → HCID 21876184, compound

HRID 724092Notes

Reaction equation

HRID 724092 reaction equation
[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]2[N:6]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH2:18]O)=[CH:13][CH:12]=3)[C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[CH:3]=1.[C:23]([O:27][C:28]([NH:30][O:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:29])([CH3:26])([CH3:25])[CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:23]([O:27][C:28]([N:30]([O:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:18][CH2:17][C:14]1[CH:13]=[CH:12][C:11]([N:6]2[C:5]3[CH:20]=[C:21]([Cl:22])[C:2]([Cl:1])=[CH:3][C:4]=3[N:8]=[C:7]2[CH2:9][CH3:10])=[CH:16][CH:15]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2728863tert-Butyl (((1,1-dimethylethoxy)carbonyl)oxy)carbamateHCID 21875693HCID 21875693, compound

Product 1

HCID 21876184HCID 21876184, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 2-[4-(5,6-dichloro-2-ethyl-1H-benzimidazol-1-yl)phenyl]ethanol (Example 96, 100 mg, 0.3 mmol), N,O-Bis-tert-butoxycarbonylhydroxylamine (Baillie, L. C.; Batsanov, A.; Bearder, J. R.; Whiting, D. A. J. Chem. Soc. Perkin Trans. 1, 1998, 20, 3471., 140 mg, 0.6 mmol) and triphenylphosphine (158 mg, 0.6 mmol) in THF (10 mL) was added diethyl azodicarboxylate (DEAD) (0.1 mL, 0.6 mmol). The mixture was stirred under nitrogen atmosphere at room temperature for 2.5 h. The solvent was removed and the residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to afford 174 mg (quant.) of the title compound as yellow amorphous: 1H-NMR (CDCl3) δ 7.84 (1H, s), 7.46 (2H, d, J=8.4 Hz), 7.25 (2H, d, J=8.4 Hz), 7.16 (1H, s), 3.92 (2H, t, J=6.7 Hz), 3.05 (2H, t, J=6.7 Hz), 2.76 (2H, q, J=7.6 Hz), 1.56 (9H, s), 1.46 (9H, s), 1.33 (3H, t, J=7.6 Hz).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-5bc7f2c19594475e8779a4fbec61cbdd
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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