Potassium Carbonate → HCID 68466339, compound

HRID 501726Notes

Reaction equation

HRID 501726 reaction equation
[CH2:1]([N:4]([C@H:15]1[C:23]2[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[C@H:17]([NH:26]C(=O)C(F)(F)F)[CH2:16]1)[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+]>CO>[CH2:1]([N:4]([C@H:15]1[C:23]2[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[C@H:17]([NH2:26])[CH2:16]1)[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86622352HCID 86622352, compound

Product 1

HCID 68466339HCID 68466339, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step AP (3): benzyl trans-allyl(5-methoxy-3-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-inden-1-yl)carbamate (735 mg, 164 mmol) from Step AP (2) and K2CO3 (1.13 g, 8.20 mmol) were refluxed in 30 mL methanol and 3 mL H2O for 24 h. the reaction was concentrated to an oil, which was dissolved in 50 mL EtOAc and extracted three times with 50 mL brine. The organic layer was dried over Na2SO4, concentrated by rotary evaporation, and dried to give the title compound (600 mg, 100%). LC-MS (M+H)+=353.2; 1H NMR (400 MHz, CDCl3) δ ppm 1.63-1.83 (m, 1H) 2.80 (s, 1H) 3.51-3.65 (m, 1H) 3.81 (s, 3H) 3.88-4.03 (m, 1H) 4.24 (s, 1H) 4.99-5.19 (m, 4H) 5.23-5.54 (m, 1H) 5.81 (s, 1H) 6.80 (dd, J=8.31, 2.01 Hz, 1H) 6.83-6.97 (m, 1H) 7.01 (d, J=8.06 Hz, 1H) 7.18 (s, 1H) 7.26-7.41 (m, 4H).

Workup

  1. concentration3 mL H2O for 24 h. the reaction was concentrated to an oil, which
  2. dissolutionwas dissolved in 50 mL EtOAc
  3. extractionextracted three times with 50 mL brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated by rotary evaporation
  6. customdried

Sources & evidence

ORD record
ord-036b7bc1e42749febbe5b2d21edd47f0
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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