Diethyl Pyrocarbonate → (R)-3-(4-tert-Butylphenyl)-N-[1-(3-fluoro-4-methanesulfonylamino-5-vinylphenyl)ethyl]acrylamide

HRID 2358404Notes

Reaction equation

HRID 2358404 reaction equation
[NH2:1][CH:2]([C:4]1[CH:9]=[C:8]([CH:10]=[CH2:11])[C:7]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[C:6]([F:17])[CH:5]=1)[CH3:3].[C:18]([C:22]1[CH:27]=[CH:26][C:25]([CH:28]=[CH:29][C:30](O)=[O:31])=[C:24](NCCC(C)C)[CH:23]=1)([CH3:21])([CH3:20])[CH3:19].CCOC(OC(OCC)=O)=O>CN(C=O)C>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([CH:28]=[CH:29][C:30]([NH:1][C@@H:2]([C:4]2[CH:9]=[C:8]([CH:10]=[CH2:11])[C:7]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[C:6]([F:17])[CH:5]=2)[CH3:3])=[O:31])=[CH:26][CH:27]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 3051Diethyl PyrocarbonateHCID 68453138HCID 68453138, compoundHCID 68455310N-[4-(1-Aminoethyl)-2-fluoro-6-vinylphenyl]methanesulfonamide

Product 1

HCID 68457488(R)-3-(4-tert-Butylphenyl)-N-[1-(3-fluoro-4-methanesulfonylamino-5-vinylphenyl)ethyl]acrylamideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[4-(1-Aminoethyl)-2-fluoro-6-vinylphenyl]methanesulfonamide (0.7 mmol, 25.3 mg), 3-[4-tert-butyl-2-(3-methylbutylamino)phenyl]acrylic acid (0.7 mmol, 15.27 mg), DEPC (0.08 mmol, 12.75 μl), and TEA (0.14 mmol, 19.51 μl) were added in DMF. The reaction mixture was stirred for 12 hrs. The reaction mixture was purified according to similar procedure of Example 21 to yield title product (36.1 mg, 100.0%).

Workup

  1. customThe reaction mixture was purified

Sources & evidence

ORD record
ord-a1ffcc37e93841cb9a97e24b160ce650
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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