Triphenylphosphine → {4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-carbamic acid tert-butyl ester

HRID 352441Notes

Reaction equation

HRID 352441 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]1[O:21][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:19][C:18]=1[CH2:28][CH2:29]O.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>C1COCC1>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:29][CH2:28][C:18]2[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:21][C:17]=2[CH3:16])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanolHCID 2756771N-Boc-4-hydroxyaniline

Product 1

HCID 69486797{4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-carbamic acid tert-butyl esterYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 5.00 g of (4-hydroxy-phenyl)-carbamic acid tert-butyl ester, 7.28 g of 2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethan-1-ol and 9.40 g of triphenylphosphine in 100 ml of THF was added at 0° C. a solution of 7.25 g of diisopropyl azodicarboxylate in 50 ml of THF over 30 min and stirring was continued at 22° C. for 16 h. A further portion of 1.88 g of triphenylphosphine and 1.45 g of diisopropyl azodicarboxylate in 10 ml of THF was added at 0° C. and stirring was continued at 22° C. for 2 h after which time conversion was complete. The mixture was evaporated and the residue purified by chromatography (SiO2, n-hexane/AcOEt 4:1) to give 7.5 g of the title compound as a colorless solid. MS: (M+H)− 395.4.

Workup

  1. stirringstirring
  2. waitwas continued at 22° C. for 2 h
  3. customThe mixture was evaporated
  4. customthe residue purified by chromatography (SiO2, n-hexane/AcOEt 4:1)

Sources & evidence

ORD record
ord-0693dc6f3009463292a27de531fe190b
Source dataset
uspto-grants-2004_06
Patent number
US06747049B2

Reaction notes

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