Methyl Acrylate → HCID 86705260, compound

HRID 879210Notes

Reaction equation

HRID 879210 reaction equation
[OH:1][C@H:2]1[C@H:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[C:5]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])[CH2:4][C@@H:3]1[CH3:25].[C:26]([O:30][CH3:31])(=[O:29])[CH:27]=[CH2:28].C(=O)([O-])[O-].[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CC(O)(C)C.O>[C:11]([O:10][C:9]([NH:8][C@@H:7]1[CH:6]=[C:5]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])[CH2:4][C@H:3]([CH3:25])[C@H:2]1[O:1][CH2:28][CH2:27][C:26]([O:30][CH3:31])=[O:29])=[O:15])([CH3:12])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 86705249HCID 86705249, compound

Product 1

HCID 86705260HCID 86705260, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of (+/−)-tert-butyl (1R,5S,6R)-6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate (1.0 equiv.), methyl acrylate (30.0 equiv.) and CESIUM CARBONATE (1.2 equiv.) in t-BuOH (0.38 M) was stirred at 35° C. for 16 hrs. The reaction was cooled to room temperature, followed by the addition of NaHCO3(aq.) and water. The mixture was extracted with EtOAc and the combined organics were dried over MgSO4, filtered, and concentrated. The sample was purified by ISCO chromatography to yield (+/−)-methyl 3-((1R,2R,6S)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyloxy)propanoate in 48% yield. LC/MS (m/z)=436.1 (MH+), Rt=0.91 min.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe sample was purified by ISCO chromatography

Sources & evidence

ORD record
ord-f94f376484824bd39a591fb3e45849cd
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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