Benzoate → HCID 131711055, compound

HRID 1679203Notes

Reaction equation

HRID 1679203 reaction equation
[C:1]([O:9][CH2:10][C:11]1[CH2:12][S:13][C@@H:14]2[C@H:21]([NH:22][C:23](=[O:34])[C:24](=[N:31][O:32][CH3:33])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:20](=[O:35])[N:15]2[C:16]=1[C:17]([OH:19])=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[C:41]([O-])(=O)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CS(C)=O>[C:1]([O:9][CH2:10][C:11]1[CH2:12][S:13][C@@H:14]2[C@H:21]([NH:22][C:23](=[O:34])[C:24](=[N:31][O:32][CH3:33])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:20](=[O:35])[N:15]2[C:16]=1[C:17]([O:19][CH:41]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 242BenzoateHCID 1061PhosphateHCID 131711056HCID 131711056, compound

Product 1

HCID 131711055HCID 131711055, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Benzoyloxymethyl-7β-(2-methoxyimino-2-phenylacetamido)-ceph-3-em-4-carboxylic Acid (syn-isomer) as a white powder (48%) [α]D + 46.5° (c 0.9 in DMSO) λmax. (pH 6 phosphate buffer) 232.5 (ε 22,400) and 258.5 nm (ε 21.400) λmax. (Nujol) 1780 (β-lactam), 1720 and 1265 (benzoate), 1705 (CO2H), 1675 and 1532 cm-1 (CONH) τ (DMSO-d6, 100 MHz) 0.16 (doublet, J 8 Hz; NH) 4.06 (double doublet J 5 and 8 Hz; C-7H), 4.70 (doublet; J5 Hz; C-6 H), 6.03 (singlet; NOCH3), and 6.14 and 6.44 [2 doublets (branches of quartet), J 18 Hz; C-2 CH2 ].

Sources & evidence

ORD record
ord-c19df533216841819d26476f5904e189
Source dataset
uspto-grants-1978_03
Patent number
US04079178

Reaction notes

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