Dichloromethane → 3-{4-[4-(2-Amino-2-dimethylcarbamoyl-ethyl)-phenoxy]-phenyl}-propionic acid methyl ester hydrochloric acid salt

HRID 748995Notes

Reaction equation

HRID 748995 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([NH:26]C(OC(C)(C)C)=O)[C:21](=[O:25])[N:22]([CH3:24])[CH3:23])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.C(Cl)[Cl:36]>>[ClH:36].[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([NH2:26])[C:21](=[O:25])[N:22]([CH3:23])[CH3:24])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 59762818HCID 59762818, compound

Product 1

HCID 691134593-{4-[4-(2-Amino-2-dimethylcarbamoyl-ethyl)-phenoxy]-phenyl}-propionic acid methyl ester hydrochloric acid salt

Conditions

Temperature
2.5 °C

Procedure

Amide compound 5 (1.8 g) was dissolved in CH2Cl2 (30 mL) and cooled to 0-5° C. Hydrogen chloride gas was bubbled through this solution for 20 min. The bubbling was discontinued and the reaction mixture was stirred at room temperature for 2 h. The excess HCl was degassed and the CH2Cl2 was removed. The residual sticky solid was dried under vacuum without further purification to yield the crude hydrochloride salt 23 (1.5 g, quantitative yield). 1H NMR (400 MHz, DMSO-d6): 7.20 (overlapped d, J=8.4 Hz, 2H), 7.18 (overlapped d, J=8.4 Hz, 2H), 6.90 (d, J=8.8 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 4.50 (m, 1H), 3.55 (s, 3H), 2.98-3.04 (m, 3H), 2.91 (dd, J=14.0 and 8.0 Hz, 1H), 2.80 (t, J=7.2 Hz, 2H), 2.77 (s, 3H), 2.67 (s, 3H), 2.59 (t, J=7.2 Hz, 2H).

Workup

  1. customHydrogen chloride gas was bubbled through this solution for 20 min
  2. customThe excess HCl was degassed
  3. customthe CH2Cl2 was removed
  4. customThe residual sticky solid was dried under vacuum without further purification

Sources & evidence

ORD record
ord-237bb27088074af9afa3b87182c524ca
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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