Hydrochloric Acid → HCID 86638780, compound

HRID 1689587Notes

Reaction equation

HRID 1689587 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([CH:17]=[CH:18][C:19]2[C:20]([CH3:32])([CH3:31])[O:21][C:22](=[C:26]([C:29]#[N:30])[C:27]#[N:28])[C:23]=2[C:24]#[N:25])[CH:14]=[CH:13][C:12]=1[NH2:33])C.Cl.O.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[NH2:33][C:12]1[CH:13]=[CH:14][C:15]([CH:17]=[CH:18][C:19]2[C:20]([CH3:32])([CH3:31])[O:21][C:22](=[C:26]([C:29]#[N:30])[C:27]#[N:28])[C:23]=2[C:24]#[N:25])=[CH:16][C:11]=1[O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:34])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 86638781HCID 86638781, compound

Product 1

HCID 86638780HCID 86638780, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6-{2-amino-5-[2-(4-cyano-5-dicyanomethylene-2,2-dimethyl-2,5-dihydro-furan-3-yl)-vinyl]-phenoxy}-hexanoic acid ethyl ester (0.33 g, 0.71 mmol), in acetic acid (6 ml) was added 5 mls of 6M HCl. The mixture was allowed to stir at room temperature for 16 hours. After being poured into 50 mls of water, it was neutralized with a solution of saturated sodium bicarbonate and extracted with ethyl acetate. Both phases of the separatory funnel remained highly colored so solid sodium chloride was added resulting in the decoloration of the aqueous layer. The organic phase was separated and dried over magnesium sulfate and rotovapped to dryness. Purification by column chromatography (60% EtOAc, 35% Hexane, 5% EtOH) provided 6-{2-amino-5-[2-(4-cyano-5-dicyanomethylene-2,2-dimethyl-2,5-dihydro-furan-3-yl)-vinyl]-phenoxy}-hexanoic acid as a shiny green solid (0.23 g, 74%). 1H NMR (400 MHz, CDCl3) δ: 7.57 (d, 1H, J=16.0 Hz), 7.17 (dd, 1H, J=8.4 Hz, J=1.6 Hz), 7.04 (d, 1H, J=1.6 Hz), 6.79 (d, 1H, J=16.0 Hz), 6.72 (d, 1H, J=8.4 Hz), 4.12 (t, 2H, J=7.2 Hz), 2.45 (t, 2H, J=6. Hz), 1.93 (m, 2H), 1.79 (m, 8H), 1.62 (m, 2H). 13C NMR (400 MHz, CDCl3) δ: 176.65, 174.34, 174.17, 148.78, 146.49, 143.21, 127.15, 124.20, 113.86, 112.45, 112.36, 111.64, 111.13, 110.16, 109.82, 97.35, 68.62, 33.27, 30.95, 29.72, 29.28, 28.75, 26.81

Workup

  1. extractionextracted with ethyl acetate
  2. additionwas added
  3. customresulting in the decoloration of the aqueous layer
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customPurification by column chromatography (60% EtOAc, 35% Hexane, 5% EtOH)

Sources & evidence

ORD record
ord-84075e266aec467b848381dbcf17107f
Source dataset
uspto-grants-2012_04
Patent number
US08153446B2

Reaction notes

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