Trifluoroacetic acid → HCID 59215863, compound

HRID 421237Notes

Reaction equation

HRID 421237 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, compoundYield 92%

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. The reaction mixture was evaporated to dryness and the desired product was purified by SCX, eluting with MeOH. The title compound (1.1 g, y=92% over 2 steps) was isolated as a mixture of diastereoisomers (ratio ˜50/50).

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
  7. customThe reaction mixture was evaporated to dryness
  8. customthe desired product was purified by SCX
  9. washeluting with MeOH

Sources & evidence

ORD record
ord-57220bd8c9b547eb9420e2c415c9a4d6
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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