Trifluoroacetic acid → HCID 59215863, compound

HRID 2074884Notes

Reaction equation

HRID 2074884 reaction equation
[OH:1][CH2:2][C@H:3]([NH:8][C:9]([CH:11]1[CH2:16][S:15][CH2:14][CH2:13][N:12]1[C:17]([O:19]C(C)(C)C)=O)=[O:10])C(OC)=O.C(O)(C(F)(F)F)=O>ClCCl>[OH:1][CH2:2][C@H:3]1[C:17](=[O:19])[N:12]2[CH:11]([CH2:16][S:15][CH2:14][CH2:13]2)[C:9](=[O:10])[NH:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59215813HCID 59215813, compound

Product 1

HCID 59215863HCID 59215863, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude 1,1-dimethylethyl 3-({[(1S)-1-(hydroxymethyl)-2-(methyloxy)-2-oxoethyl]amino}carbonyl)-4-thiomorpholinecarboxylate (D118, 3.87 g) in 44 ml of dichloromethane were added under N2, at r.t., 22 ml of TFA. The reaction mixture was stirred at room temperature for 3 hrs. The solvents were removed under reduced pressure and the residue was purified on a SCX cartridge. The fraction eluted with 2M methanolic ammonia was evaporated to dryness and the residue was dissolved in MeOH and refluxed for 20 hrs.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was purified on a SCX cartridge
  3. washThe fraction eluted with 2M methanolic ammonia
  4. customwas evaporated to dryness
  5. dissolutionthe residue was dissolved in MeOH
  6. temperaturerefluxed for 20 hrs

Sources & evidence

ORD record
ord-12d90718b7fc4dcc8a18b6cbd4df8a86
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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