2-Tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-4-vinylnaphthalen-2-yl)acetic acid → 2-Tert-butoxy-2-(1-(4-chlorophenyl)-4-ethyl-3-methylnaphthalen-2-yl)acetic acid

HRID 514126Notes

Reaction equation

HRID 514126 reaction equation
[C:1]([O:5][CH:6]([C:10]1[C:19]([CH3:20])=[C:18]([CH:21]=[CH2:22])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]>[Rh].CCO>[C:1]([O:5][CH:6]([C:10]1[C:19]([CH3:20])=[C:18]([CH2:21][CH3:22])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 671263352-Tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-4-vinylnaphthalen-2-yl)acetic acid

Product 1

HCID 671262862-Tert-butoxy-2-(1-(4-chlorophenyl)-4-ethyl-3-methylnaphthalen-2-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-4-vinylnaphthalen-2-yl)acetic acid (5.0 mg, 12 μmol), 5% w/w Rh/Al2O3 (10 mg), and EtOH (absolute, 2.0 mL) was evacuated and purged several times (vaccuum/H2 balloon). The suspension was rapidly stirred under a balloon of H2 for 6 h. H2O (500 μL) was added and the reaction was filtered through a 0.45 micron filter. The filtrate was directly purified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA). The product-containing fractions were combined and lyophilized, giving the title compound (parent form) 1H NMR (400 MHz, DMSO-d6) δ 12.71 (s, broad, 1H), 8.13 (d, J=8.2 Hz, 1H), 7.70-7.62 (m, 2H), 7.60-7.47 (m, 2H), 7.34-7.33 (m, 2H), 7.20 (d, J=8.2 Hz, 1H), 5.06 (s, 1H), 3.40-3.20 (m, 2H), 1.25 (t, J=7.4 Hz, 3H), 0.93 (s, 9H). LCMS-ESI− (m/z): [2M-2H+Na]− calcd for C50H52Cl2NaO6: 841.3; Found: 841.3.

Workup

  1. customwas evacuated
  2. custompurged several times (vaccuum/H2 balloon)
  3. additionH2O (500 μL) was added
  4. filtrationthe reaction was filtered through a 0.45 micron
  5. filtrationfilter
  6. customThe filtrate was directly purified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-304a99d0df094648b941b29948236be5
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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