Acetic Acid → HCID 67905672, compound

HRID 373978Notes

Reaction equation

HRID 373978 reaction equation
[OH:1][CH:2]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][NH:4][C@H:5]([CH3:17])[CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=1.[ClH:26].[C:27](O)(=[O:29])[CH3:28]>>[ClH:26].[C:27]([O:1][CH:2]([CH2:18][O:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:3][NH:4][C@H:5]([CH3:17])[CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 67905488HCID 67905488, compound

Product 1

HCID 67905672HCID 67905672, compound

Procedure

0.5 g of p-[(R)-3-[[(RS)-2-hydroxy-3-phenoxypropyl]-amino]butyl]benzamide was warmed to 40° for 24 hours in 25 ml of acetic acid saturated with hydrochloric acid gas. Thereupon, the solvent was removed in vacuo and the crystalline residue was recrystallized from acetonitrile, and there was obtained p-[(R)-3-[[(RS)-2-acetoxy-3-phenoxypropyl]amino]butyl]-benzamide hydrochloride of m.p. 83°-85°, [α]D20 =-10° (c=0.6 in methanol), ε222 =15020, ε234 =13590.

Workup

  1. customThereupon, the solvent was removed in vacuo
  2. customthe crystalline residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-77496168fba94b8d8e5b40e4a0ec0446
Source dataset
uspto-grants-1992_11
Patent number
US05166218

Reaction notes

Loading…