Trifluoroacetic acid methylene chloride → HCID 131730717, compound

HRID 451896Notes

Reaction equation

HRID 451896 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:47])[NH:24][C@H:25]([C@H:33]([N:36](C)[C:37](OCC[Si](C)(C)C)=O)[CH2:34][CH3:35])[CH2:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.C(Cl)Cl.[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]>>[OH:57][C:51]([C:53]([F:56])([F:55])[F:54])=[O:52].[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:47])[NH:24][C@H:25]([C@H:33]([NH:36][CH3:37])[CH2:34][CH3:35])[CH2:26][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68713227HCID 68713227, compound

Product 1

HCID 131730717HCID 131730717, compound

Procedure

Methyl 2-((R)-(3-chlorophenyl)((R)-1-((2S,3R)-1-cyclohexyl-3-(methyl((2-(trimethylsilyl)ethoxy)carbonyl)amino)pentan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate (17 mg) was dissolved in DCM/TFA (4/1 mL) and stirred for 30 min. After concentrated, the slurry was purified through preparative HPLC to afford methyl 2-((R)-(3-chlorophenyl)((R)-1-((2S,3R)-1-cyclohexyl-3-(methylamino)pentan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate TFA salt (11.9 mg).

Workup

  1. concentrationAfter concentrated
  2. customthe slurry was purified through preparative HPLC

Sources & evidence

ORD record
ord-0f58bf169b424a12b74795d56001819e
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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