[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 → [[[cis-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-oxo-2-azetidinyl]methoxy]imino]acetic acid

HRID 247642Notes

Reaction equation

HRID 247642 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)C2C(=CC=CC=2)C1=O)([CH3:4])[CH3:3].O.[C:36]([OH:40])(=[O:39])[CH:37]=O>C1COCC1>[CH3:3][C:2]([CH3:4])([O:5][C:6]([NH:7][C@H:8]1[C:11](=[O:12])[NH:10][C@H:9]1[CH2:21][O:22][N:23]=[CH:37][C:36]([OH:40])=[O:39])=[O:34])[CH3:1]

Participants

4

Reactant 2

HCID 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 esterHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 86741904[[[cis-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-oxo-2-azetidinyl]methoxy]imino]acetic acidYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the oxyamine produced in Example 1 (637 mg, 2.75 mmol) and glyoxylic acid monohydrate (295 mg, 3.20 mmol) in THF (25 ml) was allowed to stir for 1 hour. The solvent was removed under reduced pressure and the resulting solid triturated with a solution of methanol-methylene chloride (1:20) to afford [[[cis-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-2-azetidinyl]methoxy]imino]acetic acid (630 mg, 79%): IR (KBr) 3325, 2960, 1755, 1705, 1685, 1595, 1515, 1330, 1265, and 1155 cm-1 ; NMR (DMSO-d6) δ 1.40 (9H, s), 3.86 (1H, m), 4.25 (2H, m), 4.88 (1H, dd, J=9, 5 Hz), 7.59 (1H, s), 7.65 (1H, d, J=9 Hz, exchangeable), 8.40 (1H, s, exchangeable); FAB HRMS, m/e 288.1194 (M+ calculated for C11H18O6N3 : 288.1195).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting solid triturated with a solution of methanol-methylene chloride (1:20)

Sources & evidence

ORD record
ord-7ac31f123f264b36856e06da2b6ceb0b
Source dataset
uspto-grants-1987_11
Patent number
US04709025

Reaction notes

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