Hydrochloric Acid → HCID 131710688, compound
Reaction equation
C([NH:3][C@@H:4]1[C:30](=[O:31])[N:6]2[C:7]([C:14]([O:16][CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:8]([CH2:11][S:12][CH3:13])[CH2:9][S:10][C@H:5]12)=O.[ClH:32]>>[ClH:32].[NH2:3][C@@H:4]1[C:30](=[O:31])[N:6]2[C:7]([C:14]([O:16][CH:17]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:8]([CH2:11][S:12][CH3:13])[CH2:9][S:10][C@H:5]12Participants
Procedure
The oil was digested in a mixture of peroxide-free tetrahydrofuran (120 ml.) and concentrated hydrochloric acid (30 ml.), and stirred at room temperature until thin-layer examination revealed that no diphenylmethyl 7β-formamido-3-methylthiomethylceph-3-em-4-carboxylate remained. This occurred after ~5 hours, during which time the hydrochloride salt crystallised out. The solution was refrigerated overnight, filtered, and the solid dried to give diphenylmethyl 7β-amino-3-methylthiomethylceph-3-em-4-carboxlate, hydrochloride (2.4 g.), m.p. 185°-192° (decomp.), λmax. (EtOH) 265 nm. (ε 6,850), [α]D - 24.9° (C 1.0, DMSO), νmax. (Nujol) 2620 (--N+H3), 1770 (β-lactam), 1711 (ester), and 702 cm-1 (phenyl), τ (DMSO-d6) 8.1 (3-proton singlet; --S--CH3), 6.25 (2-proton singlet; C-2 protons), 6.05, 6.35 (two 1-proton doublets, J = 18 Hz; 3-CH2 --S--), 4.70 (1-proton doublet, J = 5 Hz; 7-H), 4.5 (1-proton doublet, J = 5 Hz; 6-H), 2.9 (1-proton singlet; CHPh2), 2.45 (10-proton multiplet; aromatic protons). (Found: C, 57.3; H, 5.0; Cl, 7.9; N, 5.8; S, 13.1. C22H23ClN2O3S2 requires C, 57.2; H, 5.0; Cl, 7.7; N, 6.0; S, 13.8%).
Workup
- waitThis occurred after ~5 hours, during which time
- customthe hydrochloride salt crystallised out
- filtrationfiltered
- customthe solid dried
Sources & evidence
- ORD record
- ord-74bd3d349aa746e586a473866dc91f40
- Source dataset
- uspto-grants-1977_03
- Patent number
- US04013645
Reaction notes
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