Phenylacetylene → HCID 12173663, compound

HRID 1711996Notes

Reaction equation

O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[C:14]1([C:20]#[CH:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:22](=[C:29]1[C:34](=[O:35])[O:33][C:32]([CH3:37])([CH3:36])[O:31][C:30]1=[O:38])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O.ClCCl.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:23]1([C@H:22]([CH:29]2[C:30](=[O:38])[O:31][C:32]([CH3:36])([CH3:37])[O:33][C:34]2=[O:35])[C:21]#[C:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of copper (II) acetate monohydrate (20 mg, 0.10 mmol) in water (0.4 ml) was treated with sodium (L)-ascorbate (40 mg, 0.20 mmol), the mixture was stirred until the mixture was turned bright orange (3 min). Subsequently, (R,M)-3-{[4-(2-diphenylphosphanyl-7-methoxy-naphthalen-1-yl)-phthalazin-1-ylamino]-phenyl-methyl}-pentan-3-ol (1st diastereomer, 66.2 mg, 0.10 mmol) and phenylacetylene (0.55 ml, 5.0 mmol) were added, the resulting mixture was stirred for 10 min at 23° C., cooled to 0° C., stirred for 5 min and treated with 5-benzylidene-2,2-dimethyl-1,3-dioxane-4,6-dione (116 mg, 0.50 mmol). The reaction mixture was stirred vigorously at 0° C. for 66 hrs, diluted with dichloromethane (2 ml) and subjected directly to flash chromatography on silica gel (hexane/EtOAc 3:1→1:1) to give 110 mg of the pure title compound as a white solid. (yield: 64%)

Workup

customorange (3 min)
stirringthe resulting mixture was stirred for 10 min at 23° C.
stirringstirred for 5 min
stirringThe reaction mixture was stirred vigorously at 0° C. for 66 hrs

Sources & evidence

ORD record: ord-42e0caafc70a4aaab3e21fddb7c68460
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790882B2

Reaction notes

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