Acetic Acid → (S)-2-tert-Butoxy-2-(1-(4-chlorophenyl)-3-(dimethylaminomethyl) naphthalen-2-yl)acetic acid

HRID 514022Notes

Reaction equation

HRID 514022 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH2:22][N:23]([CH3:25])[CH3:24])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CC(O)=O>C1COCC1.CO>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH2:22][N:23]([CH3:25])[CH3:24])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 68086084(S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-((dimethyl-amino)methyl)naphthalen-2-yl)acetate

Product 1

HCID 56601917(S)-2-tert-Butoxy-2-(1-(4-chlorophenyl)-3-(dimethylaminomethyl) naphthalen-2-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-((dimethylamino)methyl)naphthalen-2-yl)acetate in THF (0.5 mL) and MeOH (0.5 mL), was added NaOH solution (2N, 100 μL). The reaction mixture was stirred at room temperature for 1 day. The reaction mixture was neutralized by HOAc and concentrated down. The residue was dissolved in MeOH and purified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA) to provide the desired product (3.7 mg). 1H-NMR: 400 MHz, (CD3OD) δ: 8.12 (s, 1H), 8.00 (d, J=4.2 Hz, 1H), 7.65-7.52 (m, 5H), 7.32-7.30 (m, 2H), 5.36 (s, 1H), 4.93 (d, J=6.8 Hz, 1H), 4.47 (d, J=7 Hz, 1H), 3.12 (s, 3H), 2.89 (s, 3H), 1.12 (s, 9H). LCMS-ESI+ (m/z): [M+H]+ calcd for C25H29C1NO3: 426.2. Found: 426.1, 428.1.

Workup

  1. concentrationconcentrated down
  2. dissolutionThe residue was dissolved in MeOH
  3. custompurified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-596cec2be62e46ffb42d3f2b6907fb7e
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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