Phenylacetylene → HCID 68505193, compound

HRID 1711998Notes

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.[CH3:22][O:23][C:24]1[CH:40]=[CH:39][C:27]([CH:28]=[C:29]2[C:34](=[O:35])[O:33][C:32]([CH3:37])([CH3:36])[O:31][C:30]2=[O:38])=[CH:26][CH:25]=1>O.ClCCl.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([C@H:28]([CH:29]2[C:34](=[O:35])[O:33][C:32]([CH3:37])([CH3:36])[O:31][C:30]2=[O:38])[C:21]#[C:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:39][CH:40]=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-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (65.6 mg, 0.25 mmol). The reaction mixture was stirred vigorously at 0° C. for 64 hrs, diluted with dichloromethane (2 ml) and subjected directly to flash chromatography on silica gel (hexane/EtOAc 3:1→1:1) to give 25 mg of the pure title compound as a white solid. (yield: 27%)

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 64 hrs

Sources & evidence

ORD record: ord-e78d30db6b574780acd247bcc898d9e7
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790882B2

Reaction notes

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