Dimethylacetylene → HCID 10529100, compound

HRID 1901450Notes

Reaction equation

HRID 1901450 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][C:41]#[C:42][CH3:43].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:40][C:41]1[C:15]2[C@H:16]([C:42]=1[CH3:43])[S:17][C@H:12]1[N:13]([C:38](=[O:39])[C@H:11]1[NH:10][C:8](=[O:9])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:14]=2[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]

Participants

5

Reactant 3

HCID 10419DimethylacetyleneHCID 81531DiisopropylethylamineHCID 10769651HCID 10769651, compound

Product 1

HCID 10529100HCID 10529100, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of p-methoxybenzyl (6R,7R)-7-phenylacetamido-3-(trifluoromethyl-sulphonyloxy)ceph-3-em-4-carboxylate (60 mg, 0.102 mmol) in dichloromethane (10 ml) was cooled to 0° C., 2-Butyne (1.2 ml, 15.3 mmol) was added followed by diisopropylethylamine (18 μl, 0.102 mmol). The mixture was stirred and allowed to warm to room temperature over 15 min. Chromatography gave the title compound (28.4 mg, 57%), (Found: M+, 490.1562. C27H26N2O5S requires M, 490.1562); νmax (CH2Cl2) 1783, 1716, 1684 cm-1 ; δH (CDCl3) 1.79 (3H, s), 1.97 (3H, s), 3.62 (2H, ABq, J 16.1), 3.79 (3H, s), 4.07 (1H, br s), 4.79 (1H, d, J 4.8), 5.21 (2H, ABq, J 11.8), 5.89 (1H, dd, J 8.6, 4.8), 6.06 (1H, d, J 8.6), 6.86 (2H, d, J 8.6), 7.30 (7H, m); δc (CDCl3) 12.5, 13.2, 43.3, 45.6, 55.3, 59.8, 62.3, 67.1, 111.8, 113.9 (2c), 127.4, 127.7, 129.2 (2c) 129.5 (2c), 130.8 (2c), 133.7, 135.4, 142.5, 149.1, 159.9, 161.4, 164.4, 171.2.

Sources & evidence

ORD record
ord-9cd9b7f9a03d4b5790a913c93d48fc0a
Source dataset
uspto-grants-1996_11
Patent number
US05578592

Reaction notes

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