Trifluoroacetic acid → Trifluoroacetic acid

HRID 470592Notes

Reaction equation

HRID 470592 reaction equation
[OH:1][C@@H:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:16]=[C:15]([C:17]4[O:21][N:20]=[C:19]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[C:18]=4[C:28]([F:31])([F:30])[F:29])[O:14][N:13]=3)=[CH:9][CH:10]=2)[O:5][CH2:4][C@@H:3]1[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]>C(Cl)Cl>[C:35]([O:34][C:33](=[O:39])[NH:32][C@H:3]1[C@@H:2]([OH:1])[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:16]=[C:15]([C:17]4[O:21][N:20]=[C:19]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[C:18]=4[C:28]([F:29])([F:30])[F:31])[O:14][N:13]=3)=[CH:9][CH:10]=2)[O:5][CH2:4]1)([CH3:38])([CH3:36])[CH3:37].[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89799729HCID 89799729, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 68034313HCID 68034313, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (3S,4R)-4-hydroxy-7-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)chroman-3-ylcarbamate (500 mg) was dissolved in 30% TFA solution in DCM (3673 μl). After 2 h the reaction mixture was concentrated to give (3R,4S)-tert-butyl-4-hydroxy-7-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)chroman-3-ylcarbamate, TFA salt (quant.): LCMS=445.0 [M+H]+; 1H NMR and HPLC as in Ex. 1.

Workup

  1. concentrationAfter 2 h the reaction mixture was concentrated

Sources & evidence

ORD record
ord-8daea02a4ac44f24a3d3ed507fe48c55
Source dataset
uspto-grants-2014_01
Patent number
US08629282B2

Reaction notes

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