Trifluoroacetic acid → HCID 86643855, compound

HRID 1968345Notes

Reaction equation

HRID 1968345 reaction equation
C(OC([NH:8][C@H:9]([C:21]([O:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[C:38]([C:39]#[N:40])=[C:37]([NH:41][CH2:42][CH2:43][CH3:44])[N:36]=[C:35]([S:45][CH2:46][C:47]3[N:48]=[C:49]([C:52]4[CH:57]=[CH:56][C:55]([Cl:58])=[CH:54][CH:53]=4)[S:50][CH:51]=3)[C:34]=2[C:59]#[N:60])=[CH:29][CH:28]=1)=[O:22])[CH2:10][CH2:11][CH2:12][NH:13]C(OC(C)(C)C)=O)=O)(C)(C)C.[F:61][C:62]([F:67])([F:66])[C:63]([OH:65])=[O:64]>ClCCl>[F:61][C:62]([F:67])([F:66])[C:63]([OH:65])=[O:64].[F:61][C:62]([F:67])([F:66])[C:63]([OH:65])=[O:64].[NH2:8][C@H:9]([C:21]([O:23][CH2:24][CH2:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[C:38]([C:39]#[N:40])=[C:37]([NH:41][CH2:42][CH2:43][CH3:44])[N:36]=[C:35]([S:45][CH2:46][C:47]3[N:48]=[C:49]([C:52]4[CH:53]=[CH:54][C:55]([Cl:58])=[CH:56][CH:57]=4)[S:50][CH:51]=3)[C:34]=2[C:59]#[N:60])=[CH:31][CH:32]=1)=[O:22])[CH2:10][CH2:11][CH2:12][NH2:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86643856HCID 86643856, compound

Product 1

HCID 86643855HCID 86643855, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

60 mg (0.068 mmol) of 2-{4-(2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(propylamino)pyridin-4-yl)phenoxy}ethyl N2, N5-bis(tert-butoxycarbonyl)-L-ornithinate (Example 20A) were initially charged in 1.8 ml dichloromethane. 0.211 ml (2.738 mmol) of trifluoroacetic acid was added, and the reaction solution was then stirred at RT overnight. The reaction solution was concentrated by evaporation and the residue was purified by preparative HPLC (acetonitrile/water+0.1% TFA). This gave 55 mg (89% of theory) of the target compound.

Workup

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

Sources & evidence

ORD record
ord-1a5ae83677564415b5923f21523acf8a
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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