3-(R)-Azido-2-(S)-[(4'-ethyl-biphenyl-4-carbonyl)-amino]-butyric acid methyl ester → 3-(R)-Amino-(S)-[(4'-ethyl-biphenyl-4-carbonyl)-amino]-butyric acid methyl ester

HRID 422963Notes

Reaction equation

HRID 422963 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@@H:4]([NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:12])[C@H:5]([N:7]=[N+]=[N-])[CH3:6]>CO>[CH3:1][O:2][C:3](=[O:27])[C@@H:4]([NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:12])[C@H:5]([NH2:7])[CH3:6]

Participants

3

Reactant 1

HCID 596972273-(R)-Azido-2-(S)-[(4'-ethyl-biphenyl-4-carbonyl)-amino]-butyric acid methyl ester

Product 1

HCID 596970443-(R)-Amino-(S)-[(4'-ethyl-biphenyl-4-carbonyl)-amino]-butyric acid methyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of biphenyl azido-Thr methyl ester (6) (244 mg, 0.67 mmol) in MeOH (10 ml) was made by sonicating until the milky precipitate cleared. After bubbling nitrogen through the reaction solution for 30 sec., 10% Pd/C was added in one portion. The reaction was stirred under nitrogen at RT. The reaction was exposed to aspirator vacuum to remove the nitrogen and then opened to the hydrogen gas at balloon pressure (˜1 atm). The reaction stirred for 3 h at which time the hydrogen was exchanged for nitrogen. The reaction was filtered through a pad of celite to remove the palladium. The celite pad was washed with MeOH (30 ml). The combined fractions of MeOH were evaporated under reduced pressure and dried in vacuo to give 225 mg (99% yield) of pure produce (7) as a white solid.

Workup

  1. customby sonicating until the milky precipitate
  2. customAfter bubbling nitrogen through the reaction solution for 30 sec
  3. addition, 10% Pd/C was added in one portion
  4. customto remove the nitrogen
  5. stirringThe reaction stirred for 3 h at which time the hydrogen
  6. filtrationThe reaction was filtered through a pad of celite
  7. customto remove the palladium
  8. washThe celite pad was washed with MeOH (30 ml)
  9. customThe combined fractions of MeOH were evaporated under reduced pressure
  10. customdried in vacuo
  11. customto give 225 mg (99% yield)

Sources & evidence

ORD record
ord-1e3624fc111a479b9cc73221c668ead9
Source dataset
uspto-grants-2012_01
Patent number
US08101640B2

Reaction notes

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