Trifluoroacetic acid → HCID 27282253, compound

HRID 2357672Notes

Reaction equation

HRID 2357672 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][N:9](C(OC(C)(C)C)=O)[CH2:10][C@@H:5]2[CH2:4][O:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:4]1[C@H:5]2[CH2:10][NH:9][CH2:8][CH2:7][N:6]2[C:2](=[O:1])[O:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 684522331,1-Dimethylethyl (8aR)-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate

Product 1

HCID 27282253HCID 27282253, compoundYield 134.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of (R)-tert-butyl 3-oxo-tetrahydro-1H-oxazolo[3,4-a]pyrazine-7(3H)-carboxylate (3.01 g, 12 mmol) in 100 mL CH2Cl2 was added TFA (75 mL, 973 mmol) dropwise. After 2 h the reaction mixture was concentrated to dryness to give a brown semi-crystalline solid, which was purified through a plug of silica gel eluting successively with hexane, Et2O, CH2Cl2 and 10% 2M NH3 in MeOH/CH2Cl2 to give 2.29 g of an orange oil. MS m/z: 143.1 [M+1].

Workup

  1. concentrationAfter 2 h the reaction mixture was concentrated to dryness
  2. customto give a brown semi-crystalline solid, which
  3. customwas purified through a plug of silica gel eluting successively with hexane, Et2O, CH2Cl2 and 10% 2M NH3 in MeOH/CH2Cl2

Sources & evidence

ORD record
ord-ba8769b5c82f4a2d8909413e2f373510
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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