Acetic Acid → HCID 59103926, compound

HRID 2417554Notes

Reaction equation

HRID 2417554 reaction equation
C(O[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]1[CH2:18][N:19]([CH2:27][C:28]([O:30]CC)=O)[C:20]([O:22]C(C)(C)C)=O)=O)C1C=CC=CC=1.[H][H].[N:35]1([C:40]([C:42]2[CH:49]=[CH:48][C:45](C=O)=[CH:44][CH:43]=2)=[O:41])[CH2:39][CH:38]=[CH:37][CH2:36]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C.[Cl:75][C:76]1[CH:84]=[CH:83][C:79](C(Cl)=O)=[CH:78][CH:77]=1>C(OCC)(=O)C.ClCCl.C(O)C.[OH-].[Na+].Cl.O1CCOCC1.[Pd]>[Cl:75][C:76]1[CH:84]=[CH:83][C:79]([C:20]([N:19]2[CH2:18][C@@H:13]3[CH2:14][CH2:15][CH2:16][CH2:17][C@@H:12]3[N:11]([CH2:9][C:45]3[CH:44]=[CH:43][C:42]([C:40]([N:35]4[CH2:36][CH:37]=[CH:38][CH2:39]4)=[O:41])=[CH:49][CH:48]=3)[C:28](=[O:30])[CH2:27]2)=[O:22])=[CH:78][CH:77]=1

Participants

15

Reactant 7

HCID 176Acetic AcidHCID 8471Triethylamine2×HCID 85014-Chlorobenzoyl chlorideHCID 5049666Sodium triacetoxyborohydrideHCID 226325974-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benz-aldehydeHCID 86589890HCID 86589890, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59103926HCID 59103926, compound

Reagents, catalysts & solvents 7

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent5×HCID 8857Ethyl AcetateSolvent2×HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

225 mg (0.5 mmol) of ethyl [(((1S,2S)-2-(((benzyloxy)carbonyl)amino)cyclohexyl)methyl)(t-butoxycarbonyl)-amino]acetate was dissolved in 10 ml of ethyl acetate. 30 mg of 10% palladium/carbon was added to the obtained solution, and they were stirred in the presence of hydrogen at room temperature overnight. The reaction solution was filtered through Celite. The solvent was evaporated, and the obtained crude product was dissolved in 10 ml of dichloromethane. 121 mg (0.67 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzaldehyde and 0.065 ml (1.14 mmol) of acetic acid were added to the obtained solution, and they were stirred at room temperature for 30 minutes. 310 mg (1.4 mmol) of sodium triacetoxyborohydride was added to the reaction mixture, and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in a mixture of 2 ml of ethanol and 2 ml of 1 N sodium hydroxide, and the obtained solution was stirred at room temperature for 4 hours. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 5 ml of dichloromethane. 84 mg (0.5 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.14 ml (1.0 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 5 ml of 4N solution of hydrogen chloride in dioxane and the obtained solution was stirred at room temperature for 2 hours. The solvent was evaporated, and the obtained crude product was dissolved in 5 ml of dichloromethane. 0.062 ml (0.5 mmol) of 4-chlorobenzoyl chloride and 0.14 ml (1.0 mmol) of triethylamine were added to the obtained solution, and they were stirred at room temperature for 4 hours. The solvent was evaporated, and the obtained crude product was treated in the same manner as in step 3 in Example 1 to obtain the title compound.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. customThe solvent was evaporated
  3. customthe obtained crude product
  4. stirringwere stirred at room temperature overnight
  5. stirringthe obtained solution was stirred at room temperature for 4 hours
  6. stirringwere stirred overnight
  7. stirringthe obtained solution was stirred at room temperature for 2 hours
  8. customThe solvent was evaporated
  9. customthe obtained crude product
  10. stirringwere stirred at room temperature for 4 hours
  11. customThe solvent was evaporated
  12. customthe obtained crude product
  13. additionwas treated in the same manner as in step 3 in Example 1

Sources & evidence

ORD record
ord-1894ec1a3e5f417faa53b3067dfd210e
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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