Hydrochloric Acid → HCID 9864811, compound

HRID 1421301Notes

Reaction equation

HRID 1421301 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[C:9]([O:16][CH2:17][CH3:18])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40])(OCC)=O.Cl>CCOCC.C(#N)C.O>[CH2:17]([O:16][C:9]1[CH:8]=[C:7]([CH:2]([N:1]2[C:34](=[O:35])[C:33]3=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]3[C:31]2=[O:40])[CH2:3][C:4]([OH:6])=[O:5])[CH:12]=[CH:11][C:10]=1[O:13][CH2:14][CH3:15])[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 10586976HCID 10586976, compound

Product 1

HCID 9864811HCID 9864811, compoundYield 124.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a stirred solution of 3-amino-3-(3,4-diethoxyphenyl)propionic acid (1.03 g, 4.07 mmol) and sodium carbonate (0.453 g, 4.27 mmol) in a 1/1 mixture of 150 mL of acetonitrile/water (heated to 45° C. to dissolve) was added N-carbethoxyphthalimide (0.89 g, 4.07 mmol). The reaction mixture was stirred 1 hour, then partially concentrated in vacuo to remove the acetonitrile to afford a pale yellow solution. The stirred solution was acidified to pH 0-1 with 4 N hydrochloric acid to form a gum. The mixture was stirred overnight. The gum had not solidified and 1 mL of ether was added to mixture. The gum solidified on stirring and the slurry was filtered and the solid dried to afford 1.94 g (94%) of 3-(3,4-diethoxyphenyl)-3-phthalimidopropionic acid as a yellow solid: 1H NMR (DMSO-d6, 250 MHz) 12.41 (br s, 1H, COOH), 8.10-7.75 (m, 4H, Ar), 7.15-6.85 (m, 3H, Ar), 5.62 (overlapping dd, 1H), 4.20-3.90 (m, 4H, 2OCH2), 3.51 (dd, 1H, J=16.5, 9 Hz), 3.25 (dd, 1H, J=16.5, 7 Hz), 1.5-0.9 (m, 6H, 2 CH3) 13C NM (DMSO-d6) 1717, 167.6, 147.9, 147.8, 134.6, 131.3, 131.0, 123.1, 119.4, 113.2, 112.7, 63.8, 63.7, 50.0, 36.0, 14.6, 14.6; Anal. Calcd for C21H21NO6 : Theory C, 65.79; H, 5.52; N, 3.65. Found: C, 65.54; H, 5.55; N, 3.62.

Workup

  1. concentrationpartially concentrated in vacuo
  2. customto remove the acetonitrile
  3. customto afford a pale yellow solution
  4. customto form a gum
  5. stirringThe mixture was stirred overnight
  6. stirringon stirring
  7. filtrationthe slurry was filtered
  8. customthe solid dried

Sources & evidence

ORD record
ord-59b49eb58fab4ace8076c797c6d3bf87
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

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