Lithium Chloride → Methyl 3-benzyloxycarbonylamino-4-(1-pentynyl)benzoate

HRID 278063Notes

Reaction equation

HRID 278063 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:9][C:8]=1[NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])(=O)=O.[C:30]([Sn](CCCC)(CCCC)CCCC)#[C:31][CH2:32][CH2:33][CH3:34].[Cl-].[Li+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:21]([O:20][C:18]([NH:17][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:7]=1[C:30]#[C:31][CH2:32][CH2:33][CH3:34])[C:13]([O:15][CH3:16])=[O:14])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 11002807Stannane, tributyl-1-pentynyl-HCID 226274432-Benzyloxycarbonylamino-4-methoxycarbonylphenyl trifluoromethanesulfonate

Product 1

HCID 22627418Methyl 3-benzyloxycarbonylamino-4-(1-pentynyl)benzoateYield 65.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-benzyloxycarbonylamino-4-methoxycarbonylphenyl trifluoromethanesulfonate (1.01 g), 1-pentynyl(tributyl)stannane (1.02 g), lithium chloride (0.29 g) and tetrakis(triphenylphosphine)palladium (80 mg) in dioxane (24 ml) was heated at 100° C. for 2 hours. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (4:1) to give methyl 3-benzyloxycarbonylamino-4-(1-pentynyl)benzoate (536 mg) as colorless crystals.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-b244c014566c472b9b04f18514ef5e15
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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