BOC-Ala-Gly-OBzl → (S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acid

HRID 2309173Notes

Reaction equation

HRID 2309173 reaction equation
[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:2]([C:4]([NH:6][CH2:7][C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[O:5])[CH3:3]>C(O)(=O)C.[Pd]>[NH:1]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[C@H:2]([C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5])[CH3:3]

Participants

4

Reactant 1

HCID 10980600BOC-Ala-Gly-OBzl

Product 1

HCID 192414(S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acidYield 87.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

VII (16.97 g, 50 mmol) was taken in glacial acetic acid (170 ml) and hydrogenated overnight in the presence of 10% Pd/C (1.7 g) as catalyst at 40 psi. The catalyst was filtered with the aid of celite and solvent removed under reduced pressure. The residue was taken in satd. NaHCO3 solution, extracted with EtOAC (3×), cooled, acidified to pH 2.0 and re-extracted with EtOAC (3×). The combined EtOAC extracts were washed with Satd, NaCl, and concentrated under reduced pressure. The residue was triturated with EtOAC: Pet. ether(1:1) and the precipitate obtained was filtered, washed with pet. ether and dried (10.9 g, yield: 87.5%), Rf4 0.52. Anal Calcd. for C10H18N2O5 ·1/2H2O: C 46.50, H 7.41, N 10.84%. Found: C 46.64, H 7.41, N 10.84%.

Workup

  1. filtrationThe catalyst was filtered with the aid of celite and solvent
  2. customremoved under reduced pressure
  3. extractionNaHCO3 solution, extracted with EtOAC (3×)
  4. temperaturecooled
  5. extractionre-extracted with EtOAC (3×)
  6. washThe combined EtOAC extracts were washed with Satd, NaCl
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with EtOAC
  9. customPet. ether(1:1) and the precipitate obtained
  10. filtrationwas filtered
  11. washwashed with pet. ether
  12. customdried (10.9 g, yield: 87.5%), Rf4 0.52

Sources & evidence

ORD record
ord-d6940657e41e43ef84b13038f5e4d1ed
Source dataset
uspto-grants-1987_09
Patent number
US04693718

Reaction notes

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