Phenylacetylene → HCID 12173658, compound

HRID 1711997Notes

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][C:23]1[CH:24]=[C:25]([CH:37]=[CH:38][CH:39]=1)[CH:26]=[C:27]1[C:32](=[O:33])[O:31][C:30]([CH3:35])([CH3:34])[O:29][C:28]1=[O:36]>O.ClCCl.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:14]1([C:20]#[C:21][C@@H:26]([CH:27]2[C:28](=[O:36])[O:29][C:30]([CH3:34])([CH3:35])[O:31][C:32]2=[O:33])[C:25]2[CH:24]=[C:23]([CH3:22])[CH:39]=[CH:38][CH:37]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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-(3-methylbenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (123 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 151 mg of the pure title compound as a white solid. (yield: 87%)

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-03ab33cc018e4e668f17c1c9365d5f6a
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790882B2

Reaction notes

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