Water → HCID 69338924, compound

HRID 2086193Notes

Reaction equation

[C:1]([O:4][CH2:5][C@H:6]([CH3:19])[CH2:7][CH:8]([NH:15][C:16](=[O:18])[CH3:17])[C:9]1[S:10][C:11](Br)=[CH:12][CH:13]=1)(=[O:3])[CH3:2].[C:20]1([CH2:26][CH2:27][CH2:28][C:29]#[CH:30])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.O>CN(C)C=O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][CH2:5][C@H:6]([CH3:19])[CH2:7][CH:8]([NH:15][C:16](=[O:18])[CH3:17])[C:9]1[S:10][C:11]([C:30]#[C:29][CH2:28][CH2:27][CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

(2R)-Acetylamino-2-methyl-4-(5-bromothiophen-2-yl)butyl acetate (1.60 g, 4.59 mmol) obtained in Example 47(c) was dissolved in dimethylformamide (16 ml), and 5-phenylpent-1-yne (1.99 g, 13.8 mmol), triethylamine (6.40 ml, 45.9 mmol), copper(I) iodide (175 mg, 0.92 mmol), and dichlorobis(triphenylphosphine)palladium (322 mg, 0.46 mmol) were added thereto followed by stirring for 2 hours at 80° C. under a nitrogen atmosphere. The reaction solution was poured into water, extracted with ethyl acetate, and after the ethyl acetate layer was dried over anhydrous magnesium sulfate, the solvent was evaporated in vacuo. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=2:1-2:3) to give the title compound (1.41 g, 75% yield).

Workup

extractionextracted with ethyl acetate
dry with materialafter the ethyl acetate layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated in vacuo
customThe residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=2:1-2:3)

Sources & evidence

ORD record: ord-842ca4f600ed46f6bead3679961f8757
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06723745B2

Reaction notes

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