Trifluoroacetic acid methylene chloride → ethylcarbamate TFA salt

HRID 2039961Notes

Reaction equation

[CH2:1]([NH:3][C:4](=[O:6])[O-:5])[CH3:2].C(Cl)Cl.[C:10]([OH:16])([C:12]([F:15])([F:14])[F:13])=[O:11]>>[OH:16][C:10]([C:12]([F:15])([F:14])[F:13])=[O:11].[CH2:1]([NH:3][C:4](=[O:5])[OH:6])[CH3:2]

Participants

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chloride

HCID 22042200N-ethylcarbamate

Product 1

HCID 87968577ethylcarbamate TFA saltYield 54%

Procedure

The 2-((R)—((R)-1-((S)-2-(Boc-amino)-3-(R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)(3-chlorophenyl)methoxy)ethylcarbamate (5 mg, 0.008 mmol) was dissolved in DCM/TFA (3/1 mL). The solution was stirred for 30 min and concentrated. The crude mixture was purified on preparative HPLC to afford 2-((R)—((R)-1-(S)-2-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)(3-chlorophenyl)methoxy)ethylcarbamate TFA salt 2.8 mg, yield 54%. 1H NMR (CD3OD) δ 7.36-7.32 (m, 3H), 7.23 (d, J=7.6 Hz, 1H), 4.20 (br d, J=13.6 Hz, 1H), 4.04 (d, J=8.8 Hz, 1H), 3.89-3.78 (m, 3H), 3.64 (s, 3H), 3.48-3.42 (m, 2H), 3.37 (m, 1H), 3.28-3.24 (m, 5H), 3.15 (dd, J=10.8, 9.2 Hz, 1H), 2.92 (m, 2H), 1.97 (m, 1H), 1.78 (m, 2H), 1.68-1.54 (m, 4H), 1.45-1.07 (m, 5H). MS ESI+ve m/z 511 (M+H).

Workup

concentrationconcentrated
customThe crude mixture was purified on preparative HPLC

Sources & evidence

ORD record: ord-8e2f282d0685405a810371abc0142924
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580823B2

Reaction notes

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