Diethyl Pyrocarbonate → HCID 67243317, compound

HRID 2423345Notes

Reaction equation

HRID 2423345 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([CH3:16])[C:13]([OH:15])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:17][C@@H:18]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[C:22]([F:31])[CH:21]=1)[CH3:19].CCOC(OC(OCC)=O)=O>CN(C=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[C:12]([CH3:16])[C:13]([NH:17][CH:18]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[C:22]([F:31])[CH:21]=2)[CH3:19])=[O:15])=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 3051Diethyl PyrocarbonateHCID 543675503-(4-tert-Butylphenyl)-2-methylprop-2-enoic acidHCID 66841090HCID 66841090, compound

Product 1

HCID 67243317HCID 67243317, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-t-Butyl-phenyl)-2-methylacrylic acid (1.1 eq, 0.14 mmol, 31.00 mg) and (R)-N-[4-(1-Amino-ethyl)-2-fluorophenyl]methanesulfonamide (1 eq, 0.13 mmol, 30 mg) were dissolved in DMF. DEPC (1.2 eq, 0.16 mmol, 23.67 μl) and TEA (2 eq, 0.26 mmol, 36.24 μl) were added into the mixture. The reaction mixture was stirred for 12 hrs. DMF was removed in vacuo. The residue was extracted with ethyl acetate and H2O. A combined organic layer was washed with brine, dried with Na2SO4, and concentrated in vacuo. The residue was purified with column chromatography (n-Hx:EtOAc=1:1) to yield the title compound (52.53 mg, 93.5%) as a white solid.

Workup

  1. customDMF was removed in vacuo
  2. extractionThe residue was extracted with ethyl acetate and H2O
  3. washA combined organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with column chromatography (n-Hx:EtOAc=1:1)

Sources & evidence

ORD record
ord-fb4676b01a724fed958b8005592315d4
Source dataset
uspto-grants-2011_06
Patent number
US07960584B2

Reaction notes

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