Chloroform → HCID 131710537, compound
Reaction equation
[Br:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[CH2:37]([P:41]([CH2:46][CH2:47][CH2:48][CH3:49])[CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH3:40].C(Cl)(Cl)Cl>C(OCC)(=O)C>[Br-:1].[C:13]1([CH:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:11][C:9]([C:8]2[N:7]3[C:25](=[O:36])[C@@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]4[S:31][CH:32]=[CH:33][CH:34]=4)[C@H:6]3[S:5][CH2:4][C:3]=2[CH2:2][P+:41]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:46][CH2:47][CH2:48][CH3:49])[CH2:37][CH2:38][CH2:39][CH3:40])=[O:10])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of diphenylmethyl 3-bromomethyl-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (583 mg.) in ethyl acetate (5 ml.) was treated with a solution of tri-n-butylphosphine (0.3 ml., ca. 2 equivalents) in ethyl acetate (2 ml.). After 10 minutes at room temperature the mixture was diluted with petroleum ether to give the phosphonium salt (690 ml.) as an amorphous solid, m.p. 65° - 70° [α]D23 - 35° (c 1.0 CHCl3), inflexion at 237 nm. (ε 12,460) and 258 nm. (ε 6,550), νmax 1770 (β-lactam), 1702 (CO2R), 1670 and 1530 (CONH) and 693 (phenyl) cm.-1 ; τ (CDCl3) 4.22 (C(7) -H dd, J 4.5, 9 Hz.), 4.93 (C(6) -H, d, J 4.5 Hz.), 5.5 to 6.1 (C(2) -CH2 and =C--CH2P+, unresolved m), 7.62 (P+CH2CHCH2CH3, m), 8.55 (P+CH2CH2CH2CH3, m) and 9.1 (P+CH2CH2CH2CH3, d, J 6 Hz.).
Sources & evidence
- ORD record
- ord-e1ca02e11c3b42dea261eb0ac4f5d9b9
- Source dataset
- uspto-grants-1978_08
- Patent number
- US04110534
Reaction notes
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