Methanol → HCID 58822697, compound

HRID 459141Notes

Reaction equation

HRID 459141 reaction equation
C([O:3][C:4](=[O:19])[C@@H:5]([O:17][CH3:18])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:16])[CH2:14]Br)=[CH:9][CH:8]=1)C.[C:20]1([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+].CO>C(#N)C.[OH-].[Na+].[Cl-].[Na+].O>[C:26]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:27]=[CH:28][C:29]([O:32][CH2:14][C:13]([C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:17][CH3:18])[C:4]([OH:3])=[O:19])=[CH:12][CH:11]=2)=[O:16])=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 887Methanol2×HCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 58822842HCID 58822842, compound

Product 1

HCID 58822697HCID 58822697, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

The title compound was prepared from a solution of (2S)-3-[4-(2-Bromo-acetyl)-phenyl]-2-methoxy-propionic acid ethyl ester (25 mg, 0.076 mmol) in acetonitrile (5 ml). 4-phenylphenol (29 mg, 0.152 mmol) and K2CO3 (31,5 mg, 0.23 mmol) were added. The solution was stirred for 30 min at 80° C. and then cooled to room temperature. The mixture was concentrated to dryness under vacuum and chromatographed in silica gel (hexanes/Ethyl ether 8:2 to 7:3). Fractions corresponding to the coupled compound were collected (Rf0.27) and concentrated to dryness. The mixture thus obtained was dissolved in 4 mL of NaOH 1N and 12 mL of Methanol and stirred at room temperature until TLC indicates the disappearance of starting material. The methanol was eliminated under vacuum and the aqueous solution diluted with 20 mL of brine and washed with diethyl ether (3×15 mL). The aqueous phase was acidulated with HCl 1N (until pH 3); extracted with ethyl acetate (3×15 mL) and the organic layer dried (MgSO4) and concentrated under vacuum. Obtained a colorless oil (9.6 mg, 32%). 1H-NMR (200.15 MHz; CDCl3): δ 7.96 (d, 2H, J=8.4), 7.55–7.23 (m, 9H), 6.99 (d, 2H, J=8.8), 5.26 (s, 2H), 4.03 (dd, 1H, J=7.3, 5.6), 3.39 (s, 3H), 3.22 (dd, 1H, J=14.3, 5.5), 3.03 (dd, 1H, J=14.3, 7.2).

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe mixture was concentrated to dryness under vacuum
  3. customchromatographed in silica gel (hexanes/Ethyl ether 8:2 to 7:3)
  4. customFractions corresponding to the coupled compound were collected (Rf0.27)
  5. concentrationconcentrated to dryness
  6. customThe mixture thus obtained
  7. washwashed with diethyl ether (3×15 mL)
  8. extractionextracted with ethyl acetate (3×15 mL)
  9. dry with materialthe organic layer dried (MgSO4)
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dec2e16e7b6f4968ae2555146c9590b2
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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