Trifluoroacetic acid → HCID 57064373, compound

HRID 568288Notes

Reaction equation

HRID 568288 reaction equation
FC(F)(F)[C:3](O)=[O:4].[CH2:8]([O:11][C:12]([N:14]1[C@H:18]([C:19]2[N:20]=[C:21]([CH2:24][NH:25]OC(C)(C)C)[S:22][CH:23]=2)[CH2:17][C@@H:16]([O:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH2:15]1)=[O:13])[CH:9]=[CH2:10]>>[CH2:8]([O:11][C:12]([N:14]1[C@H:18]([C:19]2[N:20]=[C:21]([CH2:24][NH:25][CH:3]=[O:4])[S:22][CH:23]=2)[CH2:17][C@@H:16]([O:31][S:32]([CH3:35])(=[O:33])=[O:34])[CH2:15]1)=[O:13])[CH:9]=[CH2:10]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86756329HCID 86756329, compound

Product 1

HCID 57064373HCID 57064373, compound

Procedure

Trifluoroacetic acid (4 ml) is added to 1.26 g of (3R,5S)-1-allyloxycarbonyl-5-[2-(t-butoxyaminomethyl)thiazol-4-yl]-3-methanesulfonyloxypyrrolidine, and the mixture is stirred at room temperature for one hr. The reaction mixture is concentrated under reduced pressure. A saturated aqueous sodium hydrogencarbonate solution (30 ml) and 20 ml of dichloromethane are added to the residue, a mixed acid anhydride prepared from 1.0 ml of formic acid and 0.75 ml of acetic acid are added dropwise thereto, and the mixture is stirred at room temperature for one hr. The reaction mixture is subjected to separation, and the organic layer is washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent is removed by evaporation under reduced pressure. The residue is purified by column chromatography on silica gel (methanol:ethyl acetate=5:95) to give 0.81 g of (3R,5S)-1-allyloxycarbonyl-5-(2-formylaminomethylthiazol-4-yl)-3-methanesulfonyloxypyrrolidine.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additionA saturated aqueous sodium hydrogencarbonate solution (30 ml) and 20 ml of dichloromethane are added to the residue
  3. customa mixed acid anhydride prepared from 1.0 ml of formic acid and 0.75 ml of acetic acid
  4. additionare added dropwise
  5. stirringthe mixture is stirred at room temperature for one hr
  6. customThe reaction mixture is subjected to separation
  7. washthe organic layer is washed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent is removed by evaporation under reduced pressure
  10. customThe residue is purified by column chromatography on silica gel (methanol:ethyl acetate=5:95)

Sources & evidence

ORD record
ord-fb5f802a3f3a459dbe927a3ab3ddd3aa
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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