Hydrochloric Acid → HCID 25052782, compound

HRID 2382576Notes

Reaction equation

HRID 2382576 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[O:5][CH:6]1[CH2:9][N:8]([C:10]([CH3:30])([CH3:29])[CH2:11][CH2:12][C:13]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([NH2:16])=[O:15])[CH2:7]1.[ClH:34]>CO>[ClH:34].[OH:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[O:5][CH:6]1[CH2:7][N:8]([C:10]([CH3:29])([CH3:30])[CH2:11][CH2:12][C:13]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([NH2:16])=[O:15])[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16065403931409-24-4

Product 1

HCID 25052782HCID 25052782, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 5-[3-(3-Hydroxy-phenoxy)-azetidin-1-yl]-5-methyl-2,2-diphenyl-hexanoic acid amide (3.5 g, 7.8 mmol) in methanol (30 ml) was added a 1.25M HCl solution in methanol (6.3 ml, 7.8 mmol). The solution was stirred at rt for 3 h then placed in an ice bath for 6 h. As no precipitation was noticed, the solution was concentrated under reduced pressure to remove some solvent (17 ml) and the resulting solution stirred at rt for 16 h to afford a precipitate. The suspension was filtered, washed with methanol (10 ml) and dried in a vacuum oven at 40° C. to give 5-[3-(3-Hydroxy-phenoxy)-azetidin-1-yl]-5-methyl-2,2-diphenyl-hexanoic acid amide hydrochloride as a white solid, 2.55 g (67%).

Workup

  1. waitthen placed in an ice bath for 6 h
  2. customAs no precipitation
  3. concentrationthe solution was concentrated under reduced pressure
  4. customto remove some solvent (17 ml)
  5. stirringthe resulting solution stirred at rt for 16 h
  6. customto afford a precipitate
  7. filtrationThe suspension was filtered
  8. washwashed with methanol (10 ml)
  9. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-16470871bc204110838b05dd3e94c631
Source dataset
uspto-grants-2012_09
Patent number
US08263583B2

Reaction notes

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