Hydrochloric Acid → HCID 10159915, compound

HRID 584955Notes

Reaction equation

HRID 584955 reaction equation
[CH3:1][N:2]([CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([C:30]([O:32]C)=O)[C:26]([O:28]C)=[O:27])=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[Na+].[Na+].Cl.[NH2:41][OH:42].Cl>O1CCCC1.CO>[OH:42][NH:41][C:30](=[O:32])[CH:25]([CH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][N:2]([CH3:1])[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:4])[CH:13]=2)=[CH:23][CH:22]=1)[C:26]([OH:28])=[O:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 10182075HCID 10182075, compound

Product 1

HCID 10159915HCID 10159915, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 130 mg (0.3 mmol) of dimethyl 2-(3′{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-ylmethyl)malonate (prepared in Example 15(b)), 2 ml of methanol, 2 ml of tetrahydrofuran, 480 mg of sodium carbonate (4.5 mmol) and 200 mg (1.5 mmol) of hydroxylamine hydrochloride is heated at 60° C. for 18 hours. The reaction medium is neutralized to pH 6-7 with hydrochloric acid solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica, eluted with a mixture of heptane and ethyl acetate (75/25). 90 mg (72%) of the desired product, with a melting point of 60° C., are obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a mixture of heptane and ethyl acetate (75/25)

Sources & evidence

ORD record
ord-79e7b6125e1d4116855c337f929b845f
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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