Acetate → (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-[2-(carbamoylamino)-2-oxoethoxy]imino-2-(furan-2-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Reaction equation
I[CH2:2][C:3]([NH:5][C:6]([NH2:8])=[O:7])=[O:4].[Na+].[C:10]([O:13][CH2:14][C:15]1[CH2:16][S:17][C@@H:18]2[C@H:25]([NH:26][C:27](=[O:36])/[C:28](/[C:31]3[O:32][CH:33]=[CH:34][CH:35]=3)=[N:29]\[OH:30])[C:24](=[O:37])[N:19]2[C:20]=1[C:21]([O-:23])=[O:22])(=[O:12])[CH3:11].CCO.C([O-])(=O)C>CS(C)=O>[C:10]([O:13][CH2:14][C:15]1[CH2:16][S:17][C@@H:18]2[C@H:25]([NH:26][C:27](=[O:36])/[C:28](/[C:31]3[O:32][CH:33]=[CH:34][CH:35]=3)=[N:29]\[O:30][CH2:2][C:3]([NH:5][C:6]([NH2:8])=[O:7])=[O:4])[C:24](=[O:37])[N:19]2[C:20]=1[C:21]([OH:23])=[O:22])(=[O:12])[CH3:11]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
This compound was prepared from iodoacetylurea and (6R,7R)-3-acetoxymethyl-7-[Z-2-(fur-2-yl)-2-hydroxyiminoacetamido]-ceph-3-em-4-carboxylic acid sodium salt by the method described in Example 1. λmax (EtOH) 274 nm (ε 17,300), νmax (Nujol) 3420, 3260 (--NH--, --NH2), 3700-2100 (bonded OH), 1780 (β-lactam), 1720(--CO2H, acetate), 1700, 1570, 1545 cm-1 (CONH, CONH2), τ (DMSO d6) 2.11, 3.3, 3.18 (furyl), 5.28 (--O--CH2 --), 0.09 (--CONHCO--), 2.5 (CONH2), 0.11 (CONH), 4.1 (7 H), 4.78 (6 H), 6.29, 6.51 (2--CH2), 4.95, 5.28 (3 --CH2), 7.93 (CH3CO--). Yield: 34%.
Sources & evidence
- ORD record
- ord-91be911768f14cd886067195a7eff552
- Source dataset
- uspto-grants-1980_06
- Patent number
- US04208517
Reaction notes
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