Trifluoroacetic acid → HCID 117622964, compound

HRID 57078Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=2[C:40]#[N:41])=[CH:4][C:5](=[O:32])[N:6]([CH:8]([CH2:25][C@@H:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[C:9]([NH:11][C:12]2[CH:24]=[CH:23][C:15]([C:16]([O:18]C(C)(C)C)=[O:17])=[CH:14][CH:13]=2)=[O:10])[CH:7]=1.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[C:3]([C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=2[C:40]#[N:41])=[CH:4][C:5](=[O:32])[N:6]([CH:8]([CH2:25][C@@H:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[C:9]([NH:11][C:12]2[CH:24]=[CH:23][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[O:10])[CH:7]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 117622895HCID 117622895, compound

Product 1

HCID 117622964HCID 117622964, compound

Procedure

364 mg (0.61 mmol) of tert-butyl 4-({2-[5-chloro-4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-3-[(2S)-tetrahydro-2H-pyran-2-yl]propanoyl}amino)benzoate (mixture of enantiomerically pure diastereomers 1 and 2) were hydrolysed with TFA according to General Method 2. The crude product was purified by preparative flash chromatography (silica gel 50, eluent: dichloromethane/methanol gradient). Yield: 264 mg (76% of theory)

Workup

customThe crude product was purified by preparative flash chromatography (silica gel 50, eluent: dichloromethane/methanol gradient)

Sources & evidence

ORD record: ord-f868c278ce834534b17967af004270f7
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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