Sodium Acetate → HCID 67587774, compound

HRID 1417357Notes

Reaction equation

HRID 1417357 reaction equation
[C:1]([C:9]1[CH:29]=[CH:28][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])/[CH:22]=[CH:23]\[C:24]([OH:26])=O)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[C:1]([C:9]1[CH:29]=[CH:28][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[C:21](=[O:27])[CH:22]=[CH:23][C:24]2=[O:26])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 67586747HCID 67586747, compound

Product 1

HCID 67587774HCID 67587774, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The compound can be prepared from N-[6-(4-benzoylphenoxy)-hexyl]-maleamic acid from Example 11 by reacting with acetic acid and sodium acetate according to the method described in Example 2. The desired maleimide was isolated as its monohydrate by flash column chromatography. Mp 84--6° C. (Found: C, 72.78; H, 6.28; N, 3.58%. C23H23NO3, H2O requires C, 73.19; H, 6.65; N, 3.69%). H.p.l.c. 100%. FAB ms 378 (MH+). 1H-n.m.r. (CDCl3) δ 6.9 (2H, m, aromatic), 6.6 (2H, d, CH=CH), 3.9 (2H, m, CH2), 3.5 (2H, m, CH2), 1.8 (2H, m, CH2), 1.6 (2H, m, CH2), 1.5 (2H, m, CH2), 1.3 (2H, m, CH2). λmax (CH2Cl2) 286 nm, ε 16590.

Sources & evidence

ORD record
ord-ccd51235399446c5b6cd6e4b302d3bbd
Source dataset
uspto-grants-1999_03
Patent number
US05877204

Reaction notes

Loading…