HCID 53836446, compound → HCID 53668564, compound

HRID 1078622Notes

Reaction equation

HRID 1078622 reaction equation
C([O:8][C:9]([NH:11][C@H:12]([C:22]([N:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]([OH:33])=[O:32])[C:26](=[O:34])[C@@H:25]1[CH2:35][C:36]([O:38][CH3:39])=[O:37])=[O:23])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[O:10])C1C=CC=CC=1>CO.[C].[Pd]>[C:14]([O:8][C:9]([NH:11][C@H:12]([C:22]([N:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]([OH:33])=[O:32])[C:26](=[O:34])[C@@H:25]1[CH2:35][C:36]([O:38][CH3:39])=[O:37])=[O:23])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)=[O:10])([CH3:19])([CH3:15])[CH3:13]

Participants

4

Reactant 1

HCID 53836446HCID 53836446, compound

Product 1

HCID 53668564HCID 53668564, compoundYield 185.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In 300 ml of methanol was dissolved 19 g of (S)-4-(N-benzyloxycarbonyl-O-methyl-L-tyrosyl)-3-methoxycarbonylmethyl-2-oxopiperazine-1-acetic acid. To the solution was added 2.5 g of 10% palladium-carbon, and the mixture was stirred under hydrogen atomosphere for 1.5 hour. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in a mixture of 200 ml of water and 50 ml of 1,4-dioxane, to which was added 7.36 ml of triethylamine. To the mixture was added, under ice-cooling, 8.4 g of di-t-butyl dicarbonate. The reaction mixture was adjusted to pH 2 with 5% potassium hydrogensulfate, followed by extraction with ethyl acetate and drying over anhydrous sodium sulfate. The extract solution was concentrated under reduced pressure to give 16.5 g of the title compound in a crude state as a colorless powdery product.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in a mixture of 200 ml of water and 50 ml of 1,4-dioxane, to which
  4. additionwas added 7.36 ml of triethylamine
  5. additionTo the mixture was added, under ice-
  6. temperaturecooling
  7. extractionfollowed by extraction with ethyl acetate
  8. dry with materialdrying over anhydrous sodium sulfate
  9. concentrationThe extract solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6d716f59aefd4ac2bcc2c7d302edae5d
Source dataset
uspto-grants-1996_08
Patent number
US05550131

Reaction notes

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