Trifluoroacetic acid methylene chloride → HCID 58011490, compound

HRID 218448Notes

Reaction equation

HRID 218448 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:44])=[C:6]([C@@H:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:43])[NH:24][CH2:25][C@@H:26]([N:34](C(OC(C)(C)C)=O)[CH3:35])[CH2:27][C@H:28]3[CH2:33][CH2:32][CH2:31][O:30][CH2:29]3)[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:7]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:44])=[C:6]([C@@H:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:43])[NH:24][CH2:25][C@@H:26]([NH:34][CH3:35])[CH2:27][C@H:28]3[CH2:33][CH2:32][CH2:31][O:30][CH2:29]3)[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:7]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 58011518HCID 58011518, compound

Product 1

HCID 58011490HCID 58011490, compoundYield 9%

Conditions

Temperature
0 °C

Procedure

A 25 mL flask was charged with methyl 2-((R)-(5-chloro-2-methylphenyl)((R)-1-((S)-2-(Boc-methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate (60 mg, 0.094 mmol). 20% TFA/CH2Cl2 solution (8 mL) was added and stirred for 0.5 h at 0° C. The mixture was concentrated to give the residue, which was purified by preparative HPLC to give the desired product methyl 2-((R)-(5-chloro-2-methylphenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate (4.35 mg, 9%) as its TFA salt. 1H-NMR (MeOD): 1.25 (m, 2H), 1.35-1.50 (m, 4H), 1.60-1.80 (m, 3H), 1.95 (m, 2H), 2.35 (s, 3H), 2.75 (s, 3H), 3.65 (s, 3H), 3.85 (m, 4H), 4.45 (d, 1H), 7.15 (m, 2H), 7.30 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto give the residue, which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-1beb35ff38e04ce0898f589593f81934
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Reaction notes

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