Acetic Acid → HCID 23322545, compound

HRID 279792Notes

Reaction equation

HRID 279792 reaction equation
[N:1]([CH:4]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][N:6](C(C(O)=O)C)[C:5]1=[O:17])=[N+]=[N-].NC1CCCCCNC1=O.C(O)(=O)C.O=[C:33]([CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:34]([O:36][CH2:37][CH3:38])=[O:35]>C(O)C.[Pd]>[CH2:37]([O:36][C:34]([CH:33]([NH:1][CH:4]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][NH:6][C:5]1=[O:17])[CH2:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)=[O:35])[CH3:38]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 10419290HCID 10419290, compoundHCID 23322533HCID 23322533, compound

Product 1

HCID 23322545HCID 23322545, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Reduce 3-azidoperhydroazocin-2-one (Example 3) to 3-aminoperhydroazocin-2-one using 10% Pd/C in ethanol. NMR (CDCl3, TMS): δ 1.67 (broad s, 8H), δ 2.25 (broad s, 2H), δ 3.35 (m, 2H), δ 3.8 (m, 1H), δ 7.0 (broad, 1H). Hydrogenate a solution of 1.42 g of this amine, 0.59 g acetic acid and 3.09 g ethyl 2-oxo-4-phenylbutyrate in 50 ml ethanol over 10% Pd/C catalyst. AFter filtration and concentration of the reaction, purify the product by chromatography over silica gel to isolate 3-[(1-ethoxycarbonyl-3-phenyl-1-propyl)amino]perhydroazocin-2-one.

Workup

  1. filtrationAFter filtration and concentration of the reaction
  2. custompurify the product by chromatography over silica gel

Sources & evidence

ORD record
ord-647e49f7d9864e8b9ac85865314a2dc5
Source dataset
uspto-grants-1986_05
Patent number
US04587050

Reaction notes

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