Cyclohexene → HCID 10720712, compound

HRID 1901452Notes

Reaction equation

HRID 1901452 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([CH2:13][C:14]([NH:16][C@@H:17]2[C:44](=[O:45])[N:19]3[C:20]([C:32]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=4)=[O:33])=[C:21](OS(C(F)(F)F)(=O)=O)[CH2:22][S:23][C@H:18]23)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH:47]=1>ClCCl>[O:45]=[C:44]1[N:19]2[C@H:18]([S:23][C@@H:22]3[C:21](=[C:20]2[C:32]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=2)=[O:33])[C@@H:51]2[C@H:46]3[CH2:47][CH2:48][CH2:49][CH2:50]2)[C@@H:17]1[NH:16][C:14](=[O:15])[CH2:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 11430Potassium CarbonateHCID 10769651HCID 10769651, compound

Product 1

HCID 10720712HCID 10720712, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Potassium carbonate (9.5 mg, 0.068 mmol) was added to a solution of p-methoxy-benzyl (6R,7R)-7-phenylacetamido-3-(trifluoromethylsulphonyloxy)ceph-3-em-4-carboxylate (20 mg, 0.034 mmol) and cyclohexene (17.3 μl 0.17 mmol) in dichloro-methane (1.5 ml). The mixture was stirred for 16 h, then chromatographed to give the title compound (7.8 mg, 44%) as a cream solid, mp. 234°-236° C. (EtOAc) (Found: M+, 518.1882. C29H30N2O5S requires M, 518.1875); νmax (CH2Cl2) 1784, 1718, 1685 cm-1 ; δH (CDCl3) 1.00-1.99 (8H, m), 2.39 (1H, br q, J 8.2), 3.47 (1H, taut, J 9.3, 8.4, 2.6), 3.63 (2H, ABq, J 16.3), 3.80 (3H, s), 4.26 (1H, dd, J 8.7, 2.6), 4.90 (1H, d, J 4.9), 5.17 (2H, ABq, J 11.9), 5.75 (1H, dd, J 8.9, 4.9), 5.98 (1H, d, J 8.8), 6.86 (2H, d, J 8.7), 7.25-7.37 (7H, m).

Workup

  1. customchromatographed

Sources & evidence

ORD record
ord-98d5a7b7df2c422e80a690212e6a3fdb
Source dataset
uspto-grants-1996_11
Patent number
US05578592

Reaction notes

Loading…