2-Azetidinone → HCID 54407063, compound

HRID 1390409Notes

Reaction equation

HRID 1390409 reaction equation
[NH2:1][C@@H:2]1[C:17](=[O:18])[N:4]2[C:5]([C:14]([OH:16])=[O:15])=[C:6]([CH2:9][O:10][C:11](=[O:13])[NH2:12])[CH2:7][S:8][C@H:3]12.[CH3:19][O:20][N:21]=[C:22]([C:26]1[S:27][CH:28]=[CH:29][CH:30]=1)[C:23]([O-])=[O:24].[Na+].N1CCC1=O>O1CCOCC1>[C:11]([O:10][CH2:9][C:6]1[CH2:7][S:8][C@@H:3]2[C@H:2]([NH:1][C:23](=[O:24])[C:22](=[N:21][O:20][CH3:19])[C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)[C:17](=[O:18])[N:4]2[C:5]=1[C:14]([OH:16])=[O:15])(=[O:13])[NH2:12]

Participants

5

Reactant 3

HCID 1367212-AzetidinoneHCID 11391647HCID 11391647, compoundHCID 131710431HCID 131710431, compound

Product 1

HCID 54407063HCID 54407063, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following the procedure of Example 2, the title compound (888 mg., 50%) was prepared from (6R,7R)-7-amino-3-carbamoyloxymethylceph-3-em-4-carboxylic acid (1.09 g., 4 mmole) and sodium 2-methoxyimino-2-(thien-2-yl)acetate (syn -isomer) (923mg., 4.8 mmole). Its properties are: m.p. 157° to 163°, [α]D20° + 57.3° (c 1.0 in dioxan), RPAC 0.8* Solvent system A*,λmax. (pH6 buffer) 262.5 nm (ε 15,550), and inflexion at 235 nm (ε 10,350), τ (DMSO-d6) 0.20 (d, J 8 Hz, NH), 2.29 (dd, J 2 and 5 Hz, thienyl C5 -H), 2.7 to 2.9 (m, thienyl C3 -H and C4 -H), 3.40 (s, CONH2), 4.13 (dd, J 5 and 8 Hz, C7 -H), 4.75 (d, J 5 Hz, C6 -H), 5.01 and 5.34 (AB-q, J 13 Hz, C3 -CH2), 6.08 (s, NOCH3), and 6.42 (collapsed AB-q, C2 -H2), νmax. (Nujol) 3700 to 2100 (CO2H), 3480, 3440, 3365, and 3255 (NH and NH2), 1760 (azetidin-2-one), 1722 (CO2H), 1709 (OCONH2) and 1652 and 1530 cm-1 (amide).

Sources & evidence

ORD record
ord-74f62de194ee4047a24b150177f241b8
Source dataset
uspto-grants-1979_02
Patent number
US04138555

Reaction notes

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