HCID 86750090, compound → HCID 86750089, compound

HRID 619411Notes

Reaction equation

HRID 619411 reaction equation
[CH3:1][CH:2]([CH:21]([N+:29]([O-])=O)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@@H:3]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[NH:4][C:5](=[O:13])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OCC)(=O)C.[Pd]>[CH3:1][CH:2]([CH:21]([NH2:29])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@@H:3]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[NH:4][C:5](=[O:13])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 86750090HCID 86750090, compound

Product 1

HCID 86750089HCID 86750089, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of di t-butyl 3-methyl-4-nitrophenylcarbamoyl-L-glutamate (4.7 g) in ethyl acetate (125 ml) was hydrogenated over 30% Pd/C (0.5 g). The mixture obtained was then filtered through CELITE (a purified and calcined diatomaceous earth-particle size 20-45 um obtainable inter alia from Fluka Chemicals Ltd) and evaporated to a dark solid. This solid was chromatographed on silica eluted using ethyl acetate:hexane (1:1) to give di t-butyl 3-methyl-4-aminophenylcarbamoyl-L-glutamate as in oil yield=3.71 g 83%. NMR: 7.98(s)1H; 6.9(m)2H; 6.52(d)1H; 6.15(d)1H; 4.53(s)2H; 4.15(m)1H; 2.25(m)2H; 2.04(s)3H; 1.8(m)2H; 1.45(d)18H.

Workup

  1. customThe mixture obtained
  2. filtrationwas then filtered through CELITE (
  3. customa purified
  4. customevaporated to a dark solid
  5. customThis solid was chromatographed on silica
  6. washeluted

Sources & evidence

ORD record
ord-70e1e76c1f9848b08a6147df9daad76f
Source dataset
uspto-grants-1999_09
Patent number
US05958971

Reaction notes

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