Ammonium Chloride → 2-Benzyloxycarbonylamino-1-phenyl-3-butene

HRID 1813959Notes

Reaction equation

[CH2:1]([Li])CCC.[C:6]([NH:16][C@H:17]([CH:25]=O)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[NH4+].[Cl-]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:9]([O:8][C:6]([NH:16][CH:17]([CH:25]=[CH2:1])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: -29 °C

Procedure

To a stirred suspension of methyltriphenylphosphonium bromide (10.72 g, 0.03 moles) in 100 mL of dry tetrahydofuran at −78° C. was added dropwise 1.6M n-butyl lithium (17.5 mL, 0.028 moles), and the mixture was stirred for 0.5 hrs at −78-20° C. Then was added a solution of N-Cbz-phenylalaninal (5.67 g, 0.02 moles) in 50 mL of dry tetrahydrofuran, and the mixture was stirred for 16 hrs at room temperature. After addition of saturated NH4Cl (50 mL) the mixture was extracted with EtOAc, and the extract was washed with water and brine. It was dried over Na2SO4 and evaporated to give an oily residue. The crude product was purified by column chromatograpy on silica gel with elution by 5:95 EtOAc-hexane to give pure 2-benzyloxycarbonylamino-1-phenyl-3-butene.

Workup

stirringthe mixture was stirred for 16 hrs at room temperature
extractionwas extracted with EtOAc
washthe extract was washed with water and brine
dry with materialIt was dried over Na2SO4
customevaporated
customto give an oily residue
customThe crude product was purified by column chromatograpy on silica gel with elution by 5:95 EtOAc-hexane

Sources & evidence

ORD record: ord-068c1da24317429a90bc5f2a7b5aa0e2
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875776B2

Reaction notes

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