Sodium Carbonate → HCID 67212135, compound

HRID 1401893Notes

Reaction equation

HRID 1401893 reaction equation
[C:1]([O:5][C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@H:14]([C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)[C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[C:26]([CH:30]1[CH2:35][CH2:34][C:33](B(O)O)=[CH:32][CH2:31]1)([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.O>[C:1]([O:5][C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@H:14]([C:18]2[CH:23]=[CH:22][C:21]([C:33]3[CH2:34][CH2:35][CH:30]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:31][CH:32]=3)=[CH:20][CH:19]=2)[C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 44118553(4-tert-Butylcyclohex-1-en-1-yl)boronic acidHCID 67212121HCID 67212121, compound

Product 1

HCID 67212135HCID 67212135, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3.1 g of 4-[(R)-2-(4-Bromo-phenyl)-2-carboxy-ethyl-]-benzoic acid tert-butyl ester (3.Step 2, above), 1.5 g of 4-t-butyl-cyclohex-1-enyl boronic acid, 644 mg of PdCl2(P(o-tolyl)3)2, and 2.21 g of sodium carbonate in 12 mL of DME and 6 mL of ethanol and 3 mL of water was heated to reflux for a 16 h period. The reaction mixture was quenched with an excess of aqueous ammonium chloride, added ethyl acetate and the heterogeneous mixture was filtered through a celite pad. The organic phase was washed (water, saturated sodium chloride), dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel using a methanol-dichloromethane gradient to yield the carboxylic acid. HNMR (300 MHz, CDCl3, partial): 6.14 (1H, m), 1.58 (9H, s), 0.92 (9H, s). LCMS m/z=407.9 [(C30H38O4+H)—C4H9]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for a 16 h period
  3. customThe reaction mixture was quenched with an excess of aqueous ammonium chloride
  4. additionadded ethyl acetate
  5. filtrationthe heterogeneous mixture was filtered through a celite pad
  6. washThe organic phase was washed (water, saturated sodium chloride)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel using a methanol-dichloromethane gradient

Sources & evidence

ORD record
ord-7828efd123b54ecd908653a62002e68e
Source dataset
uspto-grants-2014_12
Patent number
US08907103B2

Reaction notes

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