Phenylacetylene → HCID 70001567, compound

HRID 1264426Notes

Reaction equation

HRID 1264426 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([Li])[CH2:10][CH2:11][CH3:12].C([O:18][C:19]([N:21]1[CH2:25][C@H:24]([S:26][C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][C@H:22]1[C:46](=[O:51])N(OC)C)=[O:20])CCC.OS([O-])(=O)=O.[K+]>C1COCC1>[CH2:9]([O:18][C:19]([N:21]1[CH2:25][C@H:24]([S:26][C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:23][C@H:22]1[C:46](=[O:51])[C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:20])[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 10821PhenylacetyleneHCID 516920Potassium bisulfateHCID 86585074HCID 86585074, compoundHCID 178418339Butyllithium

Product 1

HCID 70001567HCID 70001567, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 7.69 ml (70 mmol) phenylacetylen in 140 ml THF was treated at −25° C. with 43.8 ml (70 mol) n-butyllithium (1.6 M in hexane). The reaction was warmed up to −10° C. for 1 h. A solution of 7.46 g (14 mmol) (2S,4R)-2-(Methoxy-methyl-carbamoyl)-4-tritylsulfanyi-pyrrolidine-1-carboxylic acid butyl ester in 110 ml THF was then added. After 20 min the reaction was neutralized with 190 ml of an aqueous 10% KHSO4 solution. The mixture was extracted with aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous saturated 10% NaCl, dried over Na2SO4, evaporated and purified by flash-chromatography on silicagel (Hexane/EtOAc 9:1) to give 6.54 g (81%) of (2S,4R)-2-(3-Phenyl-propynoyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid butyl ester, MS: 574 (MH+).

Workup

  1. extractionThe mixture was extracted with aqueous 10% KHSO4/Et2O (3×)
  2. washThe organic phases were washed with aqueous saturated 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. custompurified by flash-chromatography on silicagel (Hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-f6786ac013014a3bbaf85658917e1106
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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