Hydrochloric Acid → HCID 66654207, compound

HRID 571802Notes

Reaction equation

HRID 571802 reaction equation
C([O:5][C:6](=[O:30])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])=[CH:17][CH:16]=2)[CH2:10]1)(C)(C)C.Cl.O1CCOCC1>>[ClH:28].[Cl:28][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:29])[C:22]=1[NH:21][C:18]1[CH:17]=[CH:16][C:15]([CH:11]2[O:12][CH2:13][CH2:14][N:9]([CH2:8][CH2:7][C:6]([OH:30])=[O:5])[CH2:10]2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66656070HCID 66656070, compound

Product 1

HCID 66654207HCID 66654207, compoundYield 173.7%

Procedure

3-{2-[4-(2,6-Dichloro-phenylamino)-phenyl]-morpholin-4-yl}-propionic acid tert-butyl ester (0.36 g; 0.80 mmol) was treated with HCl in 1,4-dioxane (3.99 mL; 4.00 mol/L; 15.95 mmol) and stirred overnight at room temperature. The solvent was removed in vacuo and the residue treated with iPr2O. The formed precipitate was collected by filtration and dried in vacuo, overnight to afford 3-{2-[4-(2,6-Dichloro-phenylamino)-phenyl]-morpholin-4-yl}-propionic acid hydrochloride (0.30 g). 1H NMR (400 MHz, DMSO-d6) □ ppm 2.83-2.98 (1H, m) 2.98-3.20 (1H, m) 3.21-3.36 (1H, m) 3.38-3.48 (1H, m) 3.49-3.55 (1H, m) 3.97 (1H, t, J=12.6 Hz) 4.04-4.18 (1H, m) 4.72 (1H, d) 6.53 (1H, d) 7.14 (1H, d) 7.29 (1H, t, J=8.1 Hz) 7.57 (1H, d) 8.03 (1H, s).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue treated with iPr2O
  3. filtrationThe formed precipitate was collected by filtration
  4. customdried in vacuo, overnight

Sources & evidence

ORD record
ord-8253d66518024cdc9d4e3f8f00306617
Source dataset
uspto-grants-2015_05
Patent number
US09029371B2

Reaction notes

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