Trifluoroacetic acid → Trifluoroacetic acid

HRID 81120Notes

Reaction equation

HRID 81120 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:6][CH2:5][O:4][C@@H:3]2[CH2:7][N:8]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:9][CH2:10][C@@H:2]12.[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29]>C(Cl)Cl>[NH:1]1[CH2:6][CH2:5][O:4][C@@H:3]2[CH2:7][N:8]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:9][CH2:10][C@@H:2]12.[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86724486(4aR,8aR)-6-benzyl 1-tert-butyl hexahydro-1H-pyrido[3,4-b][1,4]oxazine-1,6(7H)-dicarboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 86724488benzyl (4aR,8aR)-octahydro-6H-pyrido[3,4-b][1,4]oxazine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (4aR,8aR)-6-benzyl 1-tert-butyl hexahydro-1H-pyrido[3,4-b][1,4]oxazine-1,6(7H)-dicarboxylate (388 mg, 1.03 mmol) dissolved in DCM (2.8 mL) was added TFA (0.57 mL). The reaction was stirred at room temperature for 16 hours. The mixture was concentrated to afford benzyl (4aR,8aR)-octahydro-6H-pyrido[3,4-b][1,4]oxazine-6-carboxylate as a TFA salt. MS ESI calc'd. for C15H20N2O3 [M+H]+ 277. found 277.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-4224a8950ff94943bf636879af490ba0
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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