Trifluoroacetic acid → HCID 88545534, compound

HRID 403024Notes

Reaction equation

HRID 403024 reaction equation
C(OC([NH:8][C@@H:9]([CH2:74][CH:75]([CH3:77])[CH3:76])[C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17][C@@H:18]([CH2:41][O:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[C:54]([C:55]#[N:56])=[C:53]([S:57][CH2:58][C:59]3[N:60]=[C:61]([C:64]4[CH:69]=[CH:68][C:67]([Cl:70])=[CH:66][CH:65]=4)[O:62][CH:63]=3)[N:52]=[C:51]([NH2:71])[C:50]=2[C:72]#[N:73])=[CH:45][CH:44]=1)[CH2:19][O:20][C:21](=[O:40])[CH2:22][CH2:23][NH:24][C:25](=[O:39])[C@H:26]([CH2:35][CH:36]([CH3:38])[CH3:37])[NH:27]C(=O)OC(C)(C)C)=[O:16])=[O:11])=O)(C)(C)C.[F:78][C:79]([F:84])([F:83])[C:80]([OH:82])=[O:81]>ClCCl>[F:78][C:79]([F:84])([F:83])[C:80]([OH:82])=[O:81].[F:78][C:79]([F:84])([F:83])[C:80]([OH:82])=[O:81].[NH2:27][C@@H:26]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:25]([NH:24][CH2:23][CH2:22][C:21]([O:20][CH2:19][C@@H:18]([O:17][C:15](=[O:16])[CH2:14][CH2:13][NH:12][C:10](=[O:11])[C@@H:9]([NH2:8])[CH2:74][CH:75]([CH3:77])[CH3:76])[CH2:41][O:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[C:54]([C:55]#[N:56])=[C:53]([S:57][CH2:58][C:59]3[N:60]=[C:61]([C:64]4[CH:65]=[CH:66][C:67]([Cl:70])=[CH:68][CH:69]=4)[O:62][CH:63]=3)[N:52]=[C:51]([NH2:71])[C:50]=2[C:72]#[N:73])=[CH:45][CH:44]=1)=[O:40])=[O:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 88545559HCID 88545559, compound

Product 1

HCID 88545534HCID 88545534, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An amount of 85 mg (0.077 mmol) of the compound from example 33A was introduced in 0.5 ml of dichloromethane, admixed with 0.059 ml (0.771 mmol) of trifluoroacetic acid and stirred at RT overnight. The reaction mixture was then concentrated and the residue was purified by means of preparative HPLC (eluent gradient: acetonitrile/water 10:90→95:5 with addition of 0.1% TFA). This gave 47 mg (51% of theory) of the target compound.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue was purified by means of preparative HPLC (eluent gradient: acetonitrile/water 10:90→95:5 with addition of 0.1% TFA)

Sources & evidence

ORD record
ord-de3c63ab674b4bdca01e2d94cb32e735
Source dataset
uspto-grants-2014_06
Patent number
US08741834B2

Reaction notes

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