Trifluoroacetic acid → HCID 46850942, compound

HRID 1621339Notes

Reaction equation

HRID 1621339 reaction equation
C(OC([NH:8][C@H:9]([C:11]([O:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([C:29]#[N:30])=[C:27]([NH:31][CH3:32])[N:26]=[C:25]([S:33][CH2:34][C:35]3[N:36]=[C:37]([C:40]4[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=4)[S:38][CH:39]=3)[C:24]=2[C:47]#[N:48])=[CH:19][CH:18]=1)=[O:12])[CH3:10])=O)(C)(C)C.[F:49][C:50]([F:55])([F:54])[C:51]([OH:53])=[O:52]>ClCCl>[F:49][C:50]([F:55])([F:54])[C:51]([OH:53])=[O:52].[NH2:8][C@H:9]([C:11]([O:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([C:29]#[N:30])=[C:27]([NH:31][CH3:32])[N:26]=[C:25]([S:33][CH2:34][C:35]3[N:36]=[C:37]([C:40]4[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=4)[S:38][CH:39]=3)[C:24]=2[C:47]#[N:48])=[CH:19][CH:18]=1)=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59435624HCID 59435624, compound

Product 1

HCID 46850942HCID 46850942, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.18 g (3.091 mmol) of 2-{4-(2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(methylamino)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-alaninate (Example 17A) were initially charged in 45 ml of dichloromethane. 4.76 ml (61.821 mmol) of trifluoroacetic acid were added, and the reaction solution was then stirred at RT overnight. The reaction solution was concentrated on a rotary evaporator and the residue was purified by preparative HPLC (acetonitrile/water+0.1% TFA). This gave 2.04 g (92% of theory) of the target compound.

Workup

  1. concentrationThe reaction solution was concentrated on a rotary evaporator
  2. customthe residue was purified by preparative HPLC (acetonitrile/water+0.1% TFA)

Sources & evidence

ORD record
ord-e6423af95c1d494c8140bca02a66f4df
Source dataset
uspto-grants-2014_07
Patent number
US08772498B2

Reaction notes

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