Acetic Acid → HCID 67905672, compound

HRID 973760Notes

Reaction equation

HRID 973760 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-991de84d981c49bcb32ca68ceb23e8ce
Source dataset
uspto-grants-1991_11
Patent number
US05064863

Reaction notes

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