trans-2-BUTENE → HCID 10815019, compound

HRID 1901449Notes

Reaction equation

HRID 1901449 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.[CH3:40]/[CH:41]=[CH:42]/[CH3:43].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:40][C@H:41]1[C@H:42]([CH3:43])[C@H:16]2[C:15]1=[C:14]([C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)=[O:27])[N:13]1[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]1=[O:39]

Participants

5

Reactant 3

HCID 62695trans-2-BUTENEHCID 81531DiisopropylethylamineHCID 10769651HCID 10769651, compound

Product 1

HCID 10815019HCID 10815019, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of p-methoxybenzyl (6R,7R)-7-phenylacetamido-3-(trifluoromethyl-sulphonyloxy)ceph-3-em-4-carboxylate (40 mg, 0.0682 mmol) in dichloromethane (5.0 ml) was cooled to -20° C. Trans-2-butene (ca. 5 ml) was condensed into the solution. Diisopropylethylamine (12 μl, 0.068 mmol) was added and the mixture allowed to warm to room temperature over 1 h. The mixture was chromatographed to give the title compound (29.7 mg, 88%), m.p. 172°-173° C. (EtOAc) (Found: C, 65.6; H, 5.5; N, 5.6; S, 6.2; M+, 492.1724. C27H28N2O5S requires C, 65.8; H, 5.7; N, 5.7; S, 6.5%; M, 492.1719; νmax (CH2Cl2) 1786, 1721, 1687 cm-1 ; δH (CDCl3) 1.03 (3H, d, J 7.1), 1.25 (3H, d, J 7.3), 2.41 (1H, ddq, J 9.5, 7.1, 3.0), 3.04 (1H, ddq, J 7.3, 3.2, 3.0), 3.63 (2H, ABq, J 16.0), 3.79 (3H, s), 4.47 (1H, dd, J 9.5, 3.2), 4.90 (1H, d, J 4.9), 5.08 (1H, d, J 11.9), 5.26 (1H, d, J 11.9), 5.76 (1H, dd, J 9.0, 4.9), 6.07 (1H, d, J .9.0), 6.87 (2H, d, J 8.7), 7.30 (7H, m); δc (CDCl3), 15.9, 17.9, 37.2, 43.1, 43.4, 47.0, 55.3, 58.3, 59.8, 67.0, 114.0 (2c), 130.5 (2c) 121.7, 127.4, 127.7, 129.1 (2c), 129.5 (2c), 130.5 (2c), 133.8, 142.9, 159.8, 160.8, 164.2, 171.2

Workup

  1. customcondensed into the solution
  2. customThe mixture was chromatographed

Sources & evidence

ORD record
ord-5502ac97db714a1c8864a5b3e8508614
Source dataset
uspto-grants-1996_11
Patent number
US05578592

Reaction notes

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