Di-tert-butyl dicarbonate → HCID 10167009, compound

HRID 1835352Notes

Reaction equation

HRID 1835352 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C:13]([CH3:34])([CH3:33])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([C:31]#[CH:32])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[N+:37]([CH2:40][CH2:41][O:42]C1CCCCO1)([O-])=[O:38].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C.C1(C)C=CC=CC=1>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]([CH3:33])([CH3:34])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([C:31]3[O:38][N:37]=[C:40]([CH2:41][OH:42])[CH:32]=3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH3:17])=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:35])[F:36])[CH:8]=1

Participants

7

Reactant 4

HCID 90495Di-tert-butyl dicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 37486562-(2-Nitroethoxy)tetrahydropyranHCID 10278853HCID 10278853, compound

Product 1

HCID 10167009HCID 10167009, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 200 mg (0.396 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-(6-ethynyl-4-o-tolyl-pyridin-3-yl)-N-methyl-isobutyramide (Example 66), 0.182 ml (1.19 mmol) 2-(2-nitroethoxy)tetrahydropyran and 5 mg (0.04 mmol) 4-N,N-dimethylaminopyridine in 3 ml acetonitrile a solution of 260 mg (1.19 mmol) di-tert-butyl dicarbonate in 2 ml toluene was added, and the mixture was stirred at room temperature for 70 h. Quenching with water was followed by extraction with two portions of ethyl acetate. The combined organic extracts were dried with sodium sulfate and concentrated. The residue was dissolved in 1.5 ml methanol and treated with 4 mg (0.02 mmol) 4-toluenesulfonic acid monohydrate. After stirring for 1.5 h at room temperature the solvent was evaporated. The residue was dissolved in ethyl acetate. Washing with saturated sodium bicarbonate solution was followed by drying with sodium sulfate and concentration. Column chromatography afforded 35 mg (15%) of the title compound as a viscous orange oil.

Workup

  1. customQuenching with water
  2. extractionwas followed by extraction with two portions of ethyl acetate
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 1.5 ml methanol
  6. stirringAfter stirring for 1.5 h at room temperature the solvent
  7. customwas evaporated
  8. dissolutionThe residue was dissolved in ethyl acetate
  9. washWashing with saturated sodium bicarbonate solution
  10. dry with materialby drying with sodium sulfate and concentration

Sources & evidence

ORD record
ord-0ce26caf4bb3459ca50a52ca0d29342e
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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