Methyl Acrylate → HCID 131736628, compound

HRID 1481299Notes

Reaction equation

HRID 1481299 reaction equation
[NH2:1][C:2]1[C:3](I)=[CH:4][C:5]2[C:6]3[CH:7]=[CH:8][N:9]=[C:10]([CH:30]=3)[C@@H:11]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:12][CH2:13][CH2:14][C@@H:15]([CH3:21])[C:16](=[O:20])[NH:17][C:18]=2[CH:19]=1.[C:32]([O:36][CH3:37])(=[O:35])[CH:33]=[CH2:34].C(N(CCCC)CCCC)CCC>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:1][C:2]1[C:3](/[CH:34]=[CH:33]/[C:32]([O:36][CH3:37])=[O:35])=[CH:4][C:5]2[C:6]3[CH:7]=[CH:8][N:9]=[C:10]([CH:30]=3)[C@@H:11]([NH:22][C:23]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:29])[CH2:12][CH2:13][CH2:14][C@@H:15]([CH3:21])[C:16](=[O:20])[NH:17][C:18]=2[CH:19]=1

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 7622TributylamineHCID 131736627HCID 131736627, compound

Product 1

HCID 131736628HCID 131736628, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 86B (0.15 g, 0.280 mmol) in DMF (2.80 ml) was added methyl acrylate (0.048 g, 0.559 mmol), Pd(OAc)2 (2.51 mg, 0.011 mmol), and tributylamine (0.067 ml, 0.280 mmol). The reaction was microwaved at 150° C. for 10 min and the reaction was cooled to rt. The reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined organic layers were washed with water, brine, dried over Na2SO4, filtered and concentrated. Purification by normal phase chromatography afforded 86C (0.124 g, 90% yield) as a yellow solid. MS (ESI) m/z: 495.2 (M+H)+.

Workup

  1. customThe reaction was microwaved at 150° C. for 10 min
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by normal phase chromatography

Sources & evidence

ORD record
ord-cf5d9523c6e94ceab8336fd92657cb05
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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