Water → HCID 69338646, compound

HRID 1063456Notes

Reaction equation

HRID 1063456 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].[CH2:20]([OH:23])[C:21]#[CH:22].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:22]#[C:21][CH2:20][OH:23])=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 69338013HCID 69338013, compound

Product 1

HCID 69338646HCID 69338646, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(2R)-Acetylamino-2-methyl-4-(5-bromothiophen-2-yl)butyl acetate (1.38 g, 3.95 mmol) obtained in Example 47 (c) was dissolved in dimethylformamide (20 ml), and then propargylalcohol (0.69 ml, 11.9 mmol), triethylamine (5.60 ml, 40.1 mmol), copper(I) iodide (76 mg, 0.40 mmol), and dichlorobis(triphenylphosphine)palladium (276 mg, 0.39 mmol) were added thereto followed by stirring for 1 hour 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 sodium sulfate, the solvent was evaporated in vacuo. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=3:1-1:3) to afford the title compound (685 mg, 54% yield) as a white crystalline solid.

Workup

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

Sources & evidence

ORD record
ord-9afe3f62c1e945699fdb30c761edc47c
Source dataset
uspto-grants-2005_11
Patent number
US06964976B2

Reaction notes

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