Trifluoroacetic acid → H-Thz-NH-tBu

HRID 263660Notes

Reaction equation

HRID 263660 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:12][S:11][CH2:10][C@H:2]1[C:3]([NH:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].FC(F)(F)C(O)=O>>[NH:1]1[CH2:12][S:11][CH2:10][C@H:2]1[C:3]([NH:5][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:4]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54130109HCID 54130109, compound

Product 1

HCID 10535636H-Thz-NH-tBuYield 94%

Procedure

To 3.25 g (11.3 mmol) of Boc-Thz-NH-tBu, 15 ml (195 mmol) of trifluoroacetic acid was added under ice cooling and the resultant mixture was stirred at that temperature for 30 min and evaporated. The residue was washed with hexane by decantation and partitioned between chloroform and 1N NaOH aqueous solution. The organic layer was dried over Na2SO4 and evaporated under reduced pressure to give 2.00 g (Y. 94%) of H-Thz-NH-tBu which was convened to Qoa--Mta--AHPBA--Thz--NH-tBu by a similar method with processes 3-5 of Example 3.

Workup

  1. customevaporated
  2. washThe residue was washed with hexane by decantation
  3. custompartitioned between chloroform and 1N NaOH aqueous solution
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a6311746ebb44617980e9d996fa55ecc
Source dataset
uspto-grants-1997_07
Patent number
US05644028

Reaction notes

Loading…