Diethyl Ether → HCID 19426785, compound

HRID 741617Notes

Reaction equation

HRID 741617 reaction equation
[CH:1]([C:4]1[CH:24]=[CH:23][C:7]2[N:8]=[C:9]([NH:11][C@H:12]([C:20](O)=[O:21])[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:10][C:6]=2[CH:5]=1)([CH3:3])[CH3:2].[Li]C.[CH3:27]COCC.Cl[Si](C)(C)C>C1COCC1>[CH:1]([C:4]1[CH:24]=[CH:23][C:7]2[N:8]=[C:9]([NH:11][CH:12]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:20](=[O:21])[CH3:27])[S:10][C:6]=2[CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 54117434HCID 54117434, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 19426785HCID 19426785, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 g N-(6-isopropylbenzothiazol-2-yl)phenylalanine (5.9 mmol) in 60 mL THF was cooled on an ice-salt bath to -5° C., under nitrogen. A solution of 1.4N MeLi in ether (26 mL, 36.4mmol) was added via syringe over about one minute. After two hours 10 mL chlorotrimethylsilane (78 mmol) was added rapidly and the reaction warmed up to room temperature. The reaction was quenched with 1N HCl and the product extracted into ether, dried (Na2SO4) and concentrated. The product was purified by flash chromatography thru silica gel, eluting with CH2Cl2. Recrystallization from EtOH gave 0.75g product (2.2 mmol, 38%), mp 107°-110° C.

Workup

  1. customThe reaction was quenched with 1N HCl
  2. extractionthe product extracted into ether
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe product was purified by flash chromatography
  6. washeluting with CH2Cl2
  7. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-58149be8ff3b4b3ba62541d3f7de3457
Source dataset
uspto-grants-1996_09
Patent number
US05552421

Reaction notes

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