Trifluoroacetic acid → HCID 86727477, compound

HRID 519103Notes

Reaction equation

HRID 519103 reaction equation
[CH:1]([C:4]1[C:19]([O:20][C:21]2([CH3:32])[CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]2)=[CH:18][C:7]2[N:8]3[C@H:13]([CH3:14])[C:12](=[O:15])[NH:11][N:10]=[C:9]3[CH2:16][O:17][C:6]=2[CH:5]=1)([CH3:3])[CH3:2].[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[CH:1]([C:4]1[C:19]([O:20][C:21]2([CH3:32])[CH2:22][NH:23][CH2:24]2)=[CH:18][C:7]2[N:8]3[C@H:13]([CH3:14])[C:12](=[O:15])[NH:11][N:10]=[C:9]3[CH2:16][O:17][C:6]=2[CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727479HCID 86727479, compound

Product 1

HCID 86727477HCID 86727477, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 3-((8-isopropyl-1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)oxy)-3-methylazetidine-1-carboxylate ((enantiomer 2, SFC (Table 1, Method 24), Rt=9.756 min., 0.095 g, 0.213 mmol) in DCM (3 mL) was added TFA (0.5 mL) and the mixture was stirred at ambient temperature for 2 h. The solvent was removed in vacuo to give (R)-8-isopropyl-1-methyl-9-((3-methylazetidin-3-yl)oxy)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one trifluoroacetic acid (Example #121-2, Enantiomer 2, SFC (Table 1, Method 24), Rt=3.331 min, 0.085 g, 97%). LC/MS (Table 1, Method 5) Rt=2.175 min.; MS m/z: 345 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7abf95fae0eb4fdca7cf168e9b2859ee
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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