Sodium Hydroxide → HCID 178468418, compound

HRID 333419Notes

Reaction equation

HRID 333419 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([C:14]2([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:47]([N:49]([CH2:66][CH2:67][C:68]1[N:69]=[CH:70][NH:71][CH:72]=1)[C:50](=[O:65])[NH:51][CH:52]([CH2:56][C:57]1[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[CH:59][CH:58]=1)[C:53](O)=[O:54])[CH3:48].C(N(C(C)C)CC)(C)C.[OH-].[Na+]>ClCCl.CN(C)C=O>[CH:8]1([C:14]2([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:15][CH2:16][N:17]([C:53](=[O:54])[CH:52]([NH:51][C:50]([N:49]([CH2:47][CH3:48])[CH2:66][CH2:67][C:68]3[N:69]=[CH:70][NH:71][CH:72]=3)=[O:65])[CH2:56][C:57]3[CH:58]=[CH:59][C:60]([O:63][CH3:64])=[CH:61][CH:62]=3)[CH2:18][CH2:19]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66987862Ethyl 4-cyclohexylpiperidine-4-carboxylate trifluoroacetateHCID 178463865HCID 178463865, compound

Product 1

HCID 178468418HCID 178468418, compoundYield 30.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

66 mg (0.19 mmol) of ethyl 4-cyclohexylpiperidine-4-carboxylate trifluoroacetate are diluted in 3 mL of dichloromethane and 3 mL of dimethylformamide, and 67 mg (0.21 mmol) of TBTU and 75 mg (0.21 mmol) of 2-{3-ethyl-3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionic acid and 0.06 mL (0.38 mmol) of diisopropylethylamine are added. After 2 hours of stirring at room temperature, aqueous 1N NaOH solution is added and the organic products are extracted with dichloromethane. The organic phase is dried and then evaporated. The crude product obtained is chromatographed on silica gel (eluent: 95/5 dichloromethane/methanol). 34 mg of ethyl 4-cyclohexyl-1-[2-{3-ethyl-3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionyl]piperidine-4-carboxylate in the form of a yellow oil are obtained in a yield of 30%.

Workup

  1. extractionthe organic products are extracted with dichloromethane
  2. customThe organic phase is dried
  3. customevaporated
  4. customThe crude product obtained
  5. customis chromatographed on silica gel (eluent: 95/5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-711ed4cda52643c590fffc6db535f3dc
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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