Trifluoroacetic acid → Trifluoroacetic acid

HRID 1852727Notes

Reaction equation

HRID 1852727 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-c1ca51f9e2ea46c1b8e9f6ab41f05ed0
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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