Pyridine → [cis-2-[[(Acetylamino)oxy]methyl]-4-oxo-3-azetidinyl]carbamic acid 1,1-dimethylethyl ester

HRID 247641Notes

Reaction equation

HRID 247641 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:34])[NH:7][C@H:8]1[C:11](=[O:12])[N:10](C2C=CC(OC)=CC=2)[C@H:9]1[CH2:21][O:22][N:23]1C(=O)C2[C:25](=CC=CC=2)[C:24]1=[O:33])([CH3:4])[CH3:3].N1C=CC=CC=1.C(Cl)(=O)C>C(Cl)Cl.CN(C=O)C>[CH3:4][C:2]([O:5][C:6](=[O:34])[NH:7][C@H:8]1[C:11](=[O:12])[NH:10][C@H:9]1[CH2:21][O:22][NH:23][C:24](=[O:33])[CH3:25])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 13944674[cis-2-[[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]methyl]-1-(4-methoxyphenyl)-4-oxo-3-azetidinyl]carbamic acid 1,1-dimethylethyl ester

Product 1

HCID 13944682[cis-2-[[(Acetylamino)oxy]methyl]-4-oxo-3-azetidinyl]carbamic acid 1,1-dimethylethyl esterYield 88.6%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To the oxyamine produced in Example 1 (400 mg, 1.73 mmol) dissolved in a solution of CH2Cl2 -DMF (1:1) at 0° C. was added pyridine (1.1 eq.) followed by acetyl chloride (1.1 eq.). The reaction was allowed to stir for 15 minutes followed by removal of the solvents under reduced pressure. The residue obtained was purified by flash chromatography (5% CH3OH in CH2Cl2 to 10% CH3OH in CH2Cl2) to afford [cis-2-[[(acetylamino)oxy]methyl]-4-oxo-3-azetidinyl]carbamic acid 1,1-dimethylethyl ester (418 mg, 88.6%): IR (KBr) 3290, 2980, 1760, 1690, 1365, and 1160 cm-1 ; NMR (80 MHz, DMSO-d6) δ 1.40 (9H, s), 1.73 (3H, s), 3.83 (3H, m), 4.90 (1H, dd, J=9, 5 Hz), 7.60 (1H, d, J=9 Hz, exchangeable), 8.55 (1H, s, exchangeable); FAB HRMS, m/e 274.1400 (MH+ calculated for C11H20O5N3 : 274.1403).

Workup

  1. customfollowed by removal of the solvents under reduced pressure
  2. customThe residue obtained
  3. customwas purified by flash chromatography (5% CH3OH in CH2Cl2 to 10% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-a282cda9b41d4002ac420768ba11be9c
Source dataset
uspto-grants-1987_11
Patent number
US04709025

Reaction notes

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