Trifluoroacetic acid → Trifluoroacetic acid

HRID 451921Notes

Reaction equation

HRID 451921 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH:6]([CH3:46])[CH2:7][O:8][C@@H:9]([C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=1)[C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([NH:18][C@@H:19]([CH2:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[CH2:20][N:21](C)[C:22](=O)OCC[Si](C)(C)C)=[O:17])[CH2:11]1)=[O:4].[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48]>C(Cl)Cl>[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48].[Cl:45][C:41]1[CH:40]=[C:39]([C@@H:9]([C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:17])[NH:18][C@H:19]([CH2:20][NH:21][CH3:22])[CH2:32][CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)[CH2:11]2)[O:8][CH2:7][CH:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[CH3:46])[CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866394622-(trimethylsilyl)ethyl (S)-2-((R)-3-((R)-(2-(methoxycarbonylamino)propoxy)(3-chlorophenyl)methyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate

Product 2

HCID 6422Trifluoroacetic acidHCID 59201553methyl 1-((R)-(3-chlorophenyl)((R)-1-((S)-1-cyclohexyl-3-(methylamino)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)propan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(trimethylsilyl)ethyl (S)-2-((R)-3-((R)-(2-(methoxycarbonylamino)propoxy)(3-chlorophenyl)methyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate and TFA (2 mL) in CH2Cl2 (5 mL) was stirred at rt for 3 h. After the reaction mixture was evaporated under reduced pressure, the crude product was purified by reversed-phase HPLC to give TFA salt of methyl 1-((R)-(3-chlorophenyl)((R)-1-((S)-1-cyclohexyl-3-(methylamino)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)propan-2-ylcarbamate. MS ESI +ve m/z 539 (M+H).

Workup

  1. customAfter the reaction mixture was evaporated under reduced pressure
  2. customthe crude product was purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-a013c90fa189424e850b3966278752d4
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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