Ethyl oxoacetate → HCID 20244786, compound

HRID 482764Notes

Reaction equation

HRID 482764 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]([O:28][CH2:29][CH3:30])(=[O:27])[CH:25]=O>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][CH2:25][C:24]([O:28][CH2:29][CH3:30])=[O:27])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 70211Ethyl oxoacetateHCID 20244746HCID 20244746, compound

Product 1

HCID 20244786HCID 20244786, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 2-t-butyloxycarbonylamino-4-(2-aminophenyl)butyrate (10.0 g) and ethyl glyoxylate (4.2 g) in ethanol (120 ml) is hydrogenated at 80° and 3 atmospheres pressure for 72 hours using 10% palladium on charcoal (3 g) as catalyst. The reaction mixture is cooled to room temperature and the catalyst filtered off. The solvent is removed under reduced pressure and the residue distributed between ethyl acetate (150 ml) and water (75 ml). The organic phase is dried over sodium sulfate and the solvent removed under reduced pressure to give ethyl 2-t-butyloxycarbonylamino-4-[o-(ethoxycarbonylmethylamino)phenyl]butyrate which is used without further purification for the next step.

Workup

  1. customis hydrogenated at 80°
  2. filtrationthe catalyst filtered off
  3. customThe solvent is removed under reduced pressure
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-8bcc856342e845348bf19a099b2b718f
Source dataset
uspto-grants-1986_03
Patent number
US04575503

Reaction notes

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