Sodium Chloride → N,N'-di-(2-methylphenethyl)-2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonamide

HRID 2269827Notes

Reaction equation

HRID 2269827 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][S:8][C@@H:9]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]([NH:12][CH:13]([C:17](O)=[O:18])[C:14](O)=[O:15])=[O:11])=[CH:5][CH:4]=1.[Cl-].[Na+].C[N:32]1[CH2:37][CH2:36]OCC1.C[CH:39]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)CN.Cl.C(N=C=N[CH2:54][CH2:55][CH2:56][N:57](C)C)C.O.ON1[C:66]2[CH:67]=[CH:68][CH:69]=[CH:70][C:65]=2N=N1>C(OCC)(=O)C.CCCCCC.O1CCCC1.ClCCl>[CH3:68][C:67]1[CH:66]=[CH:65][CH:70]=[CH:69][C:54]=1[CH2:55][CH2:56][NH:57][C:14](=[O:15])[CH:13]([NH:12][C:10](=[O:11])[C@@H:9]([S:8][CH2:7][C:6]1[CH:27]=[CH:28][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17]([NH:32][CH2:37][CH2:36][C:47]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[CH3:39])=[O:18]

Participants

10

Reactant 6

HCID 5234Sodium ChlorideHCID 79724-MethylmorpholineHCID 113982-PhenylpropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 540116352-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonic acid

Product 1

HCID 20713092N,N'-di-(2-methylphenethyl)-2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonamide

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent2×

Procedure

Combine 2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonic acid (prepared by the method of Preparation 5, 0.476 g, 63% acid/37% sodium chloride, 0.74 mmol), and N-methylmorpholine (0.27 mL, 2.4 mmol), 2-methylphenylethylamine (0.25 mL, 1.7 mmol), dichloromethane (9 mL), and tetrahydrofuran (1mL). Add, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloric acid salt (0.314 g, 1.64 mmol) and 1 -hydroxybenztriazole hydrate (0.22 g, 1.64 mmol). After 1 day, concentrate in vacuo and partition the concentrated reaction mixture between an aqueous 5% sulfuric acid solution and ethyl acetate. Separate the layers and extract the organic layer with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 2/3 ethyl acetate/hexane and then 2/1 ethyl acetate/hexane to give the title compound.

Workup

  1. additionAdd
  2. concentrationconcentrate in vacuo
  3. custompartition
  4. customthe concentrated reaction mixture between an aqueous 5% sulfuric acid solution and ethyl acetate
  5. customSeparate the layers
  6. extractionextract the organic layer with a saturated aqueous sodium bicarbonate solution
  7. dry with materialDry the organic layer over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue

Sources & evidence

ORD record
ord-2f887d4cedd94bd399c0a67039117159
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

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