Potassium Carbonate → HCID 57429813, compound

HRID 659131

Reaction equation

HRID 659131 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][CH:10]=O)([CH3:4])([CH3:3])[CH3:2].[N+](=[C:21](P(=O)(OC)OC)C(=O)C)=[N-].C(=O)([O-])[O-].[K+].[K+]>CO>[C:12]1([CH:8]([NH:7][C:6](=[O:18])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:9][C:10]#[CH:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15087934Tert-butyl N-(3-oxo-1-phenylpropyl)carbamate2×HCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one2×

Product 1

HCID 57429813HCID 57429813, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 1.2 g of tert-butyl 3-oxo-1-phenylpropylcarbamate (Formula 12) and 1.38 g of dimethyl 1-diazo-2-oxopropylphosphonate (Formula 15) in 60 mL of methanol at 0° C. was added 1.32 g of potassium carbonate. The mixture was stirred at room temperature for 16 hours then quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. Column chromatography (5% ethyl acetate/hexane) gave 1.03 g (87%) of tert-butyl 1-phenylbut-3-ynylcarbamate (Formula 16) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.43 (s, 9H), 1.98-2.00 (m, 1H), 2.6-2.8 (m, 2H), 4.88 (br, 1H), 5.16 (br, 1H), 7.23-7.37 (m, 5H).

Workup

  1. customthen quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6e95369fee4741a88a46b9b467e411f2
Source dataset
uspto-grants-2011_12
Patent number
US08080570B2

Linked notes

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