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

HRID 247643Notes

Reaction equation

HRID 247643 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].N1C=CC=CC=1.Cl[S:42]([CH2:45][C:46]([O:48][CH3:49])=[O:47])(=[O:44])=[O:43]>C1COCC1.C(OCC)(=O)C>[CH3:49][O:48][C:46](=[O:47])[CH2:45][S:42]([NH:23][O:22][CH2:21][C@H:9]1[C@@H:8]([NH:7][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:34])[C:11](=[O:12])[NH:10]1)(=[O:44])=[O:43]

Participants

6

Reactant 3

HCID 1049PyridineHCID 11435213Methyl (chlorosulfonyl)acetateHCID 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 13944688[[[[cis-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-oxo-2-azetidinyl]methoxy]amino]sulfonyl]acetic acid methyl esterYield 54%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the oxyamine produced in Example 1 (495 mg, 2.1 mmol) in dry THF containing pyridine (1.1 eq.) was added ClSO2CH2CO2CH3 and the solution was stirred for 1 hour at 0° C. The reaction mixture was diluted with ethyl acetate and washed with 1N HCl, 5% sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. The product was purified by flash chromatography (ethyl acetate-hexane, 1:2) to afford 426 mg (54%) of [[[[cis-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-2-azetidinyl]methoxy]amino]sulfonyl]acetic acid methyl ester: mp 128°-129° C. (CH2Cl2); IR (KBr) 3340, 3210, 2975, 1780, 1740, 1685, 1525, and 1160 cm-1 ; NMR (DMSO-d6) δ 1.40 (9H, s), 3.75 (3H, s), 3.90 (1H, m), 4.00 (2H, m), 4.34 (1H, d, J=15 Hz), 4.42 (1H, d, J=15 Hz), 4.94 (1H, d, J=9, 6 Hz), 7.68 (1H, d, J=9 Hz, exchangeable), 8.44 (1H, s, exchangeable).

Workup

  1. washwashed with 1N HCl, 5% sodium bicarbonate, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe product was purified by flash chromatography (ethyl acetate-hexane, 1:2)

Sources & evidence

ORD record
ord-a0f2503db9c64d8a82a73272204f9ba5
Source dataset
uspto-grants-1987_11
Patent number
US04709025

Reaction notes

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