Acetic Acid → HCID 13135304, compound

HRID 2372591Notes

Reaction equation

HRID 2372591 reaction equation
C(O)(=O)C(O)=O.[C:7]([O:11][C:12](=[O:29])[CH2:13][N:14]([C:24](=[O:28])[C@H:25]([CH3:27])[NH2:26])[CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1)([CH3:10])([CH3:9])[CH3:8].C([O-])(=O)C.[Na+].C(O)(=O)C.O=[C:40]([CH2:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:41]([O:43][CH2:44][CH3:45])=[O:42]>C(O)C.[Ni]>[C:7]([O:11][C:12](=[O:29])[CH2:13][N:14]([C:24](=[O:28])[C@H:25]([CH3:27])[NH:26][CH:40]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1)([CH3:8])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 13132289HCID 13132289, compound

Product 1

HCID 13135304HCID 13135304, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent3×

Procedure

L-Alanyl-N-(indan-2-yl)glycine tert-butyl ester oxalate (21 g) is dissolved in 200 ml of ethanol. To the solution 4.1 g of sodium acetate, 10 ml of acetic acid, 25 g of ethyl 2-oxo-4-phenylbutyrate and 25 g of molecular sieve 3A are added in sequence. Thereafter, 30 g of Raney nickel suspended in 100 ml of ethanol is added with ethanol, and catalytic reduction is carried out under ordinary temperature and ordinary pressure. When the absorption of hydrogen has cased, the supernatant is separated by decantation, and the precipitate is washed two or three times with ethanol. The supernatant and the washings are combined and concentrated under reduced pressure. The residue is dissolved in 500 ml of ethyl acetate, and the solution is washed with aqueous sodium hydrogen carbonate and filtered with 30 g of diatomaceous earth. The ethyl acetate layer is separated from the filtrate, washed with water and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure to give 24 g of N-(1-ethoxycarbonyl- 3-phenylpropyl)-L-alanyl-N-(indan-2-yl)glycine tert-butyl ester as a slightly yellow, viscous oil.

Workup

  1. customWhen the absorption of hydrogen
  2. customthe supernatant is separated by decantation
  3. washthe precipitate is washed two or three times with ethanol
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue is dissolved in 500 ml of ethyl acetate
  6. washthe solution is washed with aqueous sodium hydrogen carbonate
  7. filtrationfiltered with 30 g of diatomaceous earth
  8. customThe ethyl acetate layer is separated from the filtrate
  9. washwashed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-9f97b7fe175c4a2a95c3f1ff01e2d4bd
Source dataset
uspto-grants-1992_03
Patent number
US05098892

Reaction notes

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