Formic Acid → Tert-butyl(2-(4-(((2R,3S)-3-amino-4-oxoazetidin-2-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl)carbamate

HRID 708475Notes

Reaction equation

HRID 708475 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([CH2:16][C@@H:17]2[C@H:20]([N:21](CC3C=CC(OC)=CC=3)C(=O)OCC3C=CC=CC=3)[C:19](=[O:41])[NH:18]2)[N:13]=[N:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)=O>CO.[Pd]>[NH2:21][C@@H:20]1[C:19](=[O:41])[NH:18][C@@H:17]1[CH2:16][C:14]1[N:13]=[N:12][N:11]([CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH:15]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 118379866Benzyl ((2R,3S)-2-((1-(2-((tert-butoxycarbonyl)amino)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-4-oxoazetidin-3-yl)(4-methoxybenzyl)carbamate

Product 1

HCID 118390234Tert-butyl(2-(4-(((2R,3S)-3-amino-4-oxoazetidin-2-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

To a slurry of benzyl ((2R,3S)-2-((1-(2-((tert-butoxycarbonyl)amino)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-4-oxoazetidin-3-yl)(4-methoxybenzyl)carbamate (20.2 mg, 0.036 mmol) in MeOH (0.68 mL) was added Pd black (19 mg, 0.018 mmol) and formic acid (31 μl, 0.711 mmol). After stirring at rt for 3 h, more Pd black (9.7 mg) was added. After stirring at rt for additional 5.5 h, the reaction mixture was filtered through cellulose with MeOH eluent, and the filtrate was concentrated in vacuo. It was used in step 6 without further purification. LCMS: Rt=0.396 min, m/z=311.1 (M+1). Method 2m_acidic.

Workup

  1. stirringAfter stirring at rt for additional 5.5 h
  2. filtrationthe reaction mixture was filtered through cellulose with MeOH eluent
  3. concentrationthe filtrate was concentrated in vacuo
  4. customIt was used in step 6 without further purification

Sources & evidence

ORD record
ord-befe30f13f10496eaeb5fd55e6650920
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

Loading…