Trifluoromethanesulfonic acid → Fmoc-Ser-OTce

HRID 491281Notes

Reaction equation

HRID 491281 reaction equation
[NH:1]([C:13]([O:15][CH2:16][CH:17]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[C@H:2]([C:5]([O:7][CH2:8][C:9]([Cl:12])([Cl:11])[Cl:10])=[O:6])[CH2:3][OH:4].Cl[C:31](Cl)(Cl)[C:32](=N)[O:33][C:34]([CH3:38])([CH3:37])[C:35]#[CH:36].[C:42](S(O)(=O)=O)(F)(F)F.ClC(Cl)(Cl)C(=N)[O-]>C(Cl)Cl.CCCCCC>[CH3:31][C:32]([O:33][C:34]([CH3:38])([CH3:37])[C:35]#[CH:36])([CH3:42])[C:2]#[CH:3].[NH:1]([C:13]([O:15][CH2:16][CH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:24]2[C:29]1=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:14])[C@H:2]([C:5]([O:7][CH2:8][C:9]([Cl:10])([Cl:11])[Cl:12])=[O:6])[CH2:3][OH:4]

Participants

7

Reactant 4

HCID 62406Trifluoromethanesulfonic acid2×HCID 10939458Fmoc-Ser-OTceHCID 111280721,1-Dimethylpropinyl trichloroacetimidateHCID 215840462,2,2-Trichloroethanimidate

Product 2

HCID 10939458Fmoc-Ser-OTceHCID 19695011Dimethylpropargyl ether

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Procedure

Fmoc-Ser-OTce (0.83 g, 1.8 mmol) was dissolved in CH2Cl2-Hexane (2:1, 4 mL), and 1,1-dimethylpropinyl trichloroacetimidate (0.41 g, 1.8 mmol, 1 equiv) and CF3SO3H (40 μl) were added under N2 atmosphere. The reaction mixture was allowed to stir for 4 days adding the same quantities of the trichloroacetimidate and CF3SO3H every 24 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo, dissolved in EtOAc (10 mL) and washed with saturated aqueous NaHCO3 (2×10 mL), H2O (2×10 mL) and brine (2×10 mL). The organic solution was dried (MgSO4) and concentrate in vacuo to obtain the 1,1-dimethylpropinyl ether of Fmoc-Ser-OTce (0.95 g), which was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutiondissolved in EtOAc (10 mL)
  4. washwashed with saturated aqueous NaHCO3 (2×10 mL), H2O (2×10 mL) and brine (2×10 mL)
  5. dry with materialThe organic solution was dried (MgSO4)
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-072af78ce7464923a69b2667086f09aa
Source dataset
uspto-grants-2009_05
Patent number
US07531506B2

Reaction notes

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