Ammonia → HCID 19810529, compound

HRID 373648Notes

Reaction equation

HRID 373648 reaction equation
[CH2:1]([CH:8]([C:22]([O:24]CC1C=CC=CC=1)=O)[CH2:9][CH2:10][CH2:11][NH:12][CH:13]([CH2:18][CH2:19][CH2:20][CH3:21])[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.CCN=C=NCCCN(C)C.C([O-])(O)=O.[Na+].N>CO.CN(C=O)C.[Pd].CCOC(C)=O>[CH2:1]([CH:8]1[CH2:9][CH2:10][CH2:11][N:12]([CH:13]([CH2:18][CH2:19][CH2:20][CH3:21])[C:14]([O:16][CH3:17])=[O:15])[C:22]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

11

Reactant 6

HCID 222AmmoniaHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 19810522HCID 19810522, compound

Product 1

HCID 19810529HCID 19810529, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The benzyl ester from Example 54 was dissolved in 10 ml of MeOH and hydrogenolyzed (H2 in balloon in the presence of 10% Pd/C, 0.3 g) at room temperature for 3 h. At the end, the catalyst was removed by filtration and the crude product, after removal of MeOH under reduced pressure, was added to a flask containing HOBT (967 mg, 7.16 mmol), Et3N (0.33 ml, 2.4 mmol) in 10 ml of DMF at 0° C. After 5 min, EDAC (458 mg, 2.38 mmol) was added and the reaction was slowly brought to room temperature. At the end of 13 h at room temperature, the contents was poured onto a slurry of aqueous NaHCO3 and AcOEt. The product was extracted and purified by Column chromatography (silica gel, Hexane-AcOEt, 4:1) which gave a mixture of two diastereomers (340 mg, 45%, 1:1 ratio, dl mixture at the benzyl centre): DCI-NH3 -MS, m/z 318 (MH+, 100%).

Workup

  1. customAt the end, the catalyst was removed by filtration
  2. customthe crude product, after removal of MeOH under reduced pressure
  3. additionwas added to a flask
  4. customwas slowly brought to room temperature
  5. extractionThe product was extracted
  6. custompurified by Column chromatography (silica gel, Hexane-AcOEt, 4:1) which
  7. customgave

Sources & evidence

ORD record
ord-5f6bc203f99e4bdbbaf96cbe19d7d7a7
Source dataset
uspto-grants-1992_11
Patent number
US05164388

Reaction notes

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