(R)-alpha-[(2-t-Butoxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, benzyl ester → (R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoic acid

HRID 1908Notes

Reaction equation

HRID 1908 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:35])([CH3:34])[C:10]([NH:12][C@H:13]([CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)[C:14]([O:16]CC1C=CC=CC=1)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:35])([CH3:34])[C:10]([NH:12][C@H:13]([CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)[C:14]([OH:16])=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86752261(R)-alpha-[(2-t-Butoxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, benzyl ester

Product 1

HCID 15895387(R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoic acidYield 102.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The benzyl ester (0.82 g, 1.71 mmol) obtained in Step C and 10% palladium on carbon (150 mg) were stirred together in ethyl acetate (5 mL). The solution was degassed and a hydrogen atmosphere introduced over the reactants using a balloon for 32 hours. The reaction products were isolated by filtering the reaction mixture through a Celite plug. The plug was washed with additional ethyl acetate (3×10 mL). The combined filtrates were evaporated under vacuum to afford the product (680 mg, 102%). 1H NMR (400 MHz, CDCl3): 1.30 (s, 9H), 1.41 (s, 6H), 3.32 (dd, 1H), 3.42 (m, 1H), 4.87 (br s, 1H), 6.82 (d, 1H), 7.13-7.35 (m, 8H), 7.60 (d, 1H), 8.28 (br s, 1H).

Workup

  1. customThe solution was degassed
  2. additiona hydrogen atmosphere introduced over the reactants
  3. customfor 32 hours
  4. customThe reaction products were isolated
  5. filtrationby filtering the reaction mixture through a Celite plug
  6. washThe plug was washed with additional ethyl acetate (3×10 mL)
  7. customThe combined filtrates were evaporated under vacuum

Sources & evidence

ORD record
ord-80904ffecdf74601af3321b00e801887
Source dataset
uspto-grants-1998_03
Patent number
US05726319

Reaction notes

Loading…