Trifluoroacetic acid → (4AR,8aR)-hexahydro-1H-pyrido[3,4-b][1,4]oxazin-2(3H)-one

HRID 1593464Notes

Reaction equation

HRID 1593464 reaction equation
[O:1]=[C:2]1[CH2:7][O:6][C@@H:5]2[CH2:8][N:9](C(OC(C)(C)C)=O)[CH2:10][CH2:11][C@H:4]2[NH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:3]1[C:2](=[O:1])[CH2:7][O:6][C@@H:5]2[CH2:8][NH:9][CH2:10][CH2:11][C@@H:4]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58745484(4aR*,8aR*)-2-oxo-octahydro-pyrido[3,4-b][1,4]oxazine-6-carboxylic acid tert-butyl ester

Product 1

HCID 58745453(4AR,8aR)-hexahydro-1H-pyrido[3,4-b][1,4]oxazin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 249C (70.0 mg, 0.0.27 mmol) in 1 mL of CH2Cl2 at room temperature was added TFA (2.00 mL, 25.9 mmol). The mixture was stirred at room temperature for 1 hr and concentrated in vacuo to give crude 249D. This material was mixed with DMA to make a 2 mL stock solution and was used as is in next step reaction.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c2f0a2d0f5544f580a9b7c684dd5b1a
Source dataset
uspto-grants-2007_11
Patent number
US07297695B2

Reaction notes

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