Methyl Acrylate → HCID 86681335, compound

HRID 403342Notes

Reaction equation

HRID 403342 reaction equation
[Br:1][C:2]1[C:3]([C@@H:8]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C@H:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=2[F:21])[CH2:10][CH2:11][CH:12]=[CH2:13])=[N:4][CH:5]=[CH:6][N:7]=1.[C:30]([O:34][CH3:35])(=[O:33])C=C>C(Cl)Cl>[Br:1][C:2]1[C:3]([C@@H:8]([NH:22][C:23]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:29])[C@H:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=2[F:21])[CH2:10][CH2:11]/[CH:12]=[CH:13]/[C:30]([O:34][CH3:35])=[O:33])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 86681336HCID 86681336, compound

Product 1

HCID 86681335HCID 86681335, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 250 mL round-bottomed flask was dissolved tert-butyl (1S,2S)-1-(3-bromopyrazin-2-yl)-2-(2,3-difluorophenyl)hex-5-enylcarbamate (354.6 mg, 0.757 mmol) in methylene chloride (16 mL) to give a colorless solution. Methyl acrylate (0.21 mL, 2.3 mmol) and Grubbs-If catalyst (32.1 mg, 0.038 mmol) were added, and the mixture was stirred under reflux for 3 h under nitrogen. TLC showed complete conversion. Volatile components were removed in vacuo and the residue was purified by flash column chromatography upto 50% ethyl acetate/hexane to afford the desired product (335 mg, 84%) as a colorless oil: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.31 (s, 1H) 8.28 (s, 1H) 6.98-7.14 (m, 3H) 6.80-6.94 (m, 1H) 5.76 (d, J=16.56 Hz, 1H) 5.59-5.71 (m, 1H) 5.42 (d, 0.1-9.54 Hz, 1H) 3.71 (s, 3H) 3.59-3.69 (m, 1H) 2.09-2.29 (m, 2H) 1.96-2.04 (m, 1H) 1.83-1.95 (m, 1H) 1.37 (s, 9H).

Workup

  1. customto give a colorless solution
  2. temperatureunder reflux for 3 h under nitrogen
  3. customVolatile components were removed in vacuo
  4. customthe residue was purified by flash column chromatography upto 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-89aa856c75154688b9cf28c979b4a5f5
Source dataset
uspto-grants-2014_06
Patent number
US08748429B2

Reaction notes

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