Ethanol → N-(9-fluorenylmethoxycarbonyl)-3-(5-bromo-2-thienyl)-L-alanine ethyl ester

HRID 24684Notes

Reaction equation

HRID 24684 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][C:21]3[S:22][C:23]([Br:26])=[CH:24][CH:25]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:30][CH2:31]O>>[CH2:30]([O:28][C:27](=[O:29])[C@H:19]([CH2:20][C:21]1[S:22][C:23]([Br:26])=[CH:24][CH:25]=1)[NH:18][C:16]([O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:17])[CH3:31]

Participants

3

Reactant 2

HCID 702EthanolHCID 7006538Fmoc-L-2-(5-bromothienyl)alanine

Product 1

HCID 54001394N-(9-fluorenylmethoxycarbonyl)-3-(5-bromo-2-thienyl)-L-alanine ethyl ester

Conditions

Temperature
50 °C

Procedure

N-(9-Fluorenylmethoxycarbonyl)-3-(5-bromo-2-thienyl)-L-alanine (813 mg) was dissolved in EtOH (15 mL) and HCl (gas) was bubbled through the solution for 5 min at 0° C. The mixture was warmed to 50° C. and stirred for 1 h. After cooling to room temperature the solvent was evaporated. The residue was purified by column chromatography (silica gel; eluent: hexane to hexane/EtOAc 1:1) provided N-(9-fluorenylmethoxycarbonyl)-3-(5-bromo-2-thienyl)-L-alanine ethyl ester (767 mg): ESMS: m/z 500 MH+.

Workup

  1. customHCl (gas) was bubbled through the solution for 5 min at 0° C
  2. temperatureAfter cooling to room temperature the solvent
  3. customwas evaporated
  4. customThe residue was purified by column chromatography (silica gel; eluent: hexane to hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-2d75f7c58b0e4ea5b2a82a14bdb9a0a0
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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