Phenylacetylene → HCID 68503211, compound

HRID 1711999Notes

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.[Br:22][C:23]1[CH:39]=[CH:38][C:26]([CH:27]=[C:28]2[C:33](=[O:34])[O:32][C:31]([CH3:36])([CH3:35])[O:30][C:29]2=[O:37])=[CH:25][CH:24]=1>O.ClCCl.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:22][C:23]1[CH:24]=[CH:25][C:26]([C@H:27]([CH:28]2[C:29](=[O:37])[O:30][C:31]([CH3:36])([CH3:35])[O:32][C:33]2=[O:34])[C:21]#[C:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:38][CH:39]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of copper (II) acetate monohydrate (10 mg, 0.050 mmol) in water (0.2 ml) was treated with sodium (L)-ascorbate (20 mg, 0.10 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, 33.1 mg, 0.050 mmol) and phenylacetylene (0.275 ml, 2.5 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-(4-bromobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (77.7 mg, 0.25 mmol). The reaction mixture was stirred vigorously at 0° C. for 42 hrs, diluted with dichloromethane (2 ml) and subjected directly to flash chromatography on silica gel (hexane/EtOAc 3:1→1:1) to give 53 mg of the pure title compound as a white solid. (Yield: 39%)

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 42 hrs

Sources & evidence

ORD record: ord-5ffbc9db60c54654a8d628cb97eeaf31
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790882B2

Reaction notes

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