Allyl Alcohol → HCID 10529227, compound

HRID 1901451Notes

Reaction equation

HRID 1901451 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:38](=[O:39])[N:13]3[C:14]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)=[O:27])=[C:15](OS(C(F)(F)F)(=O)=O)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:40]([OH:43])[CH:41]=[CH2:42].C(N(C(C)C)CC)(C)C>ClCCl>[OH:43][CH2:40][C@@H:41]1[C@H:16]2[C:15](=[C:14]([C:26]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)=[O:27])[N:13]3[C@H:12]([S:17]2)[C@H:11]([NH:10][C:8](=[O:9])[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:38]3=[O:39])[CH2:42]1

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 81531DiisopropylethylamineHCID 10769651HCID 10769651, compound

Product 1

HCID 10529227HCID 10529227, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of p-methoxybenzyl (6R,7R)-7-phenylacetamido-3-(trifluoromethylsulphonyloxy)ceph-3-em-4-carboxylate (20 mg, 0.0341 mmol), allyl alcohol (11.6 μl, 0.171 mmol) and dichloromethane (0.5 ml) was added diisopropylethyl-amine (6 μl, 0.034 mmol). After stirring at room temperature for 30 min the mixture was chromatographed to give the title compound (12 mg, 71%), (Found: M+, 4.94.1528. C26H26N2O6S requires M, 494.1512); νmax (CH2Cl2) 1787, 1722, 1687 cm-1 ; δH (CDCl3) 2.89 (1H, m), 2.96 (1H, dt, J 16.8 , 3.0), 3.22 (1H, ddd, J 16.2, 8.9, 1.2), 3.62 (2H, ABq, J 15.7), 3.65 (2H, d, J 7.2), 3.79 (3H, s), 4.44 (1H, m), 4.92 (1H, d, J 5.0), 5.17 (2H, ABq, J 12.0), 5.76 (1H, dd, J 8.9, 5.0), 6.32 (1H, d, J 8.9), 6.86 (2H, d, J 8.6), 7.28 (7H, m).

Workup

  1. customwas chromatographed

Sources & evidence

ORD record
ord-abf8c259008d47cbb321c1a3a8ec5fb8
Source dataset
uspto-grants-1996_11
Patent number
US05578592

Reaction notes

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