Sodium Carbonate → HCID 67618881, compound

HRID 2276354Notes

Reaction equation

HRID 2276354 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH:5]([OH:28])[C:6]1[C:7]([CH3:27])=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)=[CH:13][C:12]1[CH2:23][CH2:24][CH2:25][CH2:26][C:11]=1[CH:10]=2)[CH3:2].Cl(O)(=O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(OC(C)(C)C)(=O)C>[CH2:1]([O:3][C:4](=[O:29])[CH:5]([O:28][C:6]([CH3:7])([CH3:15])[CH3:5])[C:6]1[C:7]([CH3:27])=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)=[CH:13][C:12]1[CH2:23][CH2:24][CH2:25][CH2:26][C:11]=1[CH:10]=2)[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24247Perchloric AcidHCID 69673186HCID 69673186, compound

Product 1

HCID 67618881HCID 67618881, compoundYield 127.7%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

To a 50 mL flask containing a stirred suspension of hydroxy-(2-methyl-4-p-tolyl-6,7,8,9-tetrahydro-benzo[g]quinolin-3-yl)-acetic acid ethyl ester (15.3 mg, 39.0 μmol) in tert-butyl acetate (4 mL) under nitrogen was added perchloric acid (72%, 9.80 uL, 117 μmol) and the clear solution was stirred at ambient temperature for 3 hours. Added sodium carbonate solution (10%) until neutralization had occurred and extracted with ethyl acetate (10 mL). Organics were dried using a hydrophobic frit and evaporated onto silica. Chromatographed using ISCO Companion with a Redisep silica gel 4 g cartridge and a gradient of heptane and ethyl acetate (0-20%). Evaporation gave tert-butoxy-(2-methyl-4-p-tolyl-6,7,8,9-tetrahydro-benzo[g]quinolin-3-yl)-acetic acid ethyl ester as a clear oil 11.1 mg (63.8% Yield). LCMS (5 min acidic) 2.66 min 100% pure by ELSD and UV ES+ and AP+ 446. HNMR (CDCl3) >95% pure 7.76 (br-s, 1H), 7.37-7.32 (m, 3H), 7.22-7.20 (m, 1H), 7.03 (br-s, 1H), 5.14 (s, 1H), 4.21-4.15 (m, 2H), 3.00 (br-t, 2H), 2.85-2.73 (m, 5H), 2.50 (s, 3H), 1.88-1.77 (m, 4H), 1.22 (t, 3H), 0.97 (s, 9H).

Workup

  1. additionTo a 50 mL flask containing
  2. extractionextracted with ethyl acetate (10 mL)
  3. customOrganics were dried
  4. customevaporated onto silica
  5. customChromatographed
  6. customEvaporation

Sources & evidence

ORD record
ord-8c389f46916f4527b5e2e29d4348d046
Source dataset
uspto-grants-2015_09
Patent number
US09132129B2

Reaction notes

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