Triphenylphosphine → HCID 59153161, compound

HRID 2355290Notes

Reaction equation

HRID 2355290 reaction equation
[OH:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([OH:12])[CH:5]=[CH:4][C:3]=1[C:13](=[O:18])[CH2:14][CH:15]([CH3:17])[CH3:16].[C:19]([O:23][C:24](=[O:35])[NH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33]O)=[CH:29][CH:28]=1)([CH3:22])([CH3:21])[CH3:20].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>C1(C)C=CC=CC=1>[C:19]([O:23][C:24](=[O:35])[NH:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:33][O:12][C:6]2[CH:5]=[CH:4][C:3]([C:13](=[O:18])[CH2:14][CH:15]([CH3:16])[CH3:17])=[C:2]([OH:1])[C:7]=2[C:8]([F:9])([F:10])[F:11])=[CH:31][CH:32]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2794813tert-Butyl [4-(hydroxymethyl)benzyl]carbamateHCID 59153172HCID 59153172, compound

Product 1

HCID 59153161HCID 59153161, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Mix 1-(2,4-dihydroxy-3-trifluoromethyl-phenyl)-3-methyl-butan-1-one (2 g, 7.63 mmol), (4-hydroxymethyl-benzyl)-carbamic acid tert-butyl ester (1.99 g, 8.39 mmol) and triphenylphosphine (2.20 g, 8.39 mmol) in anhydrous toluene (125 mL) at room temperature under argon gas. Slowly add diisopropyl azodicarboxylate (1.70 g, 8.39 mmol, 1.7 mL) over 30 min. Stir the reaction mixture at room temperature overnight. Concentrate the mixture under reduced pressure and purify the residue by flash chromatography (silica gel) eluting with using 25% ethyl acetate/hexane to provide the product as a white solid (1.5 g, 3.12 mmol, 41% yield). MS (m/z): 480 (M−1).

Workup

  1. concentrationConcentrate the mixture under reduced pressure
  2. custompurify the residue by flash chromatography (silica gel)
  3. washeluting

Sources & evidence

ORD record
ord-24fb2410913349ff9ccc8ee4572d3792
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

Loading…