Trifluoroacetic acid → 2-(5-(4-((1R,2S)-2-amino-3-fluoro-1-hydroxypropyl)phenyl)isoxazol-3-yl)acetonitrile

HRID 1500289Notes

Reaction equation

HRID 1500289 reaction equation
[C:1]([CH2:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[O:19]C(C)(C)[N:17](C(OC(C)(C)C)=O)[C@@H:16]3[CH2:29][F:30])=[CH:11][CH:10]=2)[O:6][N:5]=1)#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[NH2:17][C@H:16]([CH2:29][F:30])[C@@H:15]([C:12]1[CH:11]=[CH:10][C:9]([C:7]2[O:6][N:5]=[C:4]([CH2:3][C:1]#[N:2])[CH:8]=2)=[CH:14][CH:13]=1)[OH:19]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86713175(4S,5R)-tert-butyl 5-(4-(3-(cyanomethyl)isoxazol-5-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 867131762-(5-(4-((1R,2S)-2-amino-3-fluoro-1-hydroxypropyl)phenyl)isoxazol-3-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

The product of step 1 of Example 12 (50 mg, 0.12 mmol) in CH2Cl2 (2 mL) at 5° C. is treated with trifluoroacetic acid (0.5 mL), stirred 30 minutes at room temperature, diluted with toluene, and concentrated to give the title compound, which is carried on to the next step without purification m/z (Cl) 276 [M+H].

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-c52ff02eea9b4601800a495da71c1689
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

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