Trifluoroacetic acid → HCID 131731435, compound

HRID 403022Notes

Reaction equation

HRID 403022 reaction equation
C(OC([NH:8][C@@H:9]([CH2:82][CH2:83][CH2:84][CH2:85][NH:86]C(OC(C)(C)C)=O)[C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17][C@@H:18]([CH2:49][O:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]2[C:62]([C:63]#[N:64])=[C:61]([S:65][CH2:66][C:67]3[N:68]=[C:69]([C:72]4[CH:77]=[CH:76][C:75]([Cl:78])=[CH:74][CH:73]=4)[O:70][CH:71]=3)[N:60]=[C:59]([NH2:79])[C:58]=2[C:80]#[N:81])=[CH:53][CH:52]=1)[CH2:19][O:20][C:21](=[O:48])[CH2:22][CH2:23][NH:24][C:25](=[O:47])[C@@H:26]([NH:39]C(OC(C)(C)C)=O)[CH2:27][CH2:28][CH2:29][CH2:30][NH:31]C(=O)OC(C)(C)C)=[O:16])=[O:11])=O)(C)(C)C.[F:94][C:95]([F:100])([F:99])[C:96]([OH:98])=[O:97]>ClCCl>[F:94][C:95]([F:100])([F:99])[C:96]([OH:98])=[O:97].[F:94][C:95]([F:100])([F:99])[C:96]([OH:98])=[O:97].[F:94][C:95]([F:100])([F:99])[C:96]([OH:98])=[O:97].[F:94][C:95]([F:100])([F:99])[C:96]([OH:98])=[O:97].[NH2:39][C@@H:26]([CH2:27][CH2:28][CH2:29][CH2:30][NH2:31])[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])[CH2:82][CH2:83][CH2:84][CH2:85][NH2:86])[CH2:49][O:50][C:51]1[CH:52]=[CH:53][C:54]([C:57]2[C:62]([C:63]#[N:64])=[C:61]([S:65][CH2:66][C:67]3[N:68]=[C:69]([C:72]4[CH:77]=[CH:76][C:75]([Cl:78])=[CH:74][CH:73]=4)[O:70][CH:71]=3)[N:60]=[C:59]([NH2:79])[C:58]=2[C:80]#[N:81])=[CH:55][CH:56]=1)=[O:48])=[O:47]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 88545523HCID 88545523, compound

Product 1

HCID 131731435HCID 131731435, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An amount of 70 mg (0.058 mmol) of the compound from example 31A was introduced in 0.5 ml of dichloromethane, admixed with 0.045 ml (0.578 mmol) of trifluoroacetic acid and stirred at RT. After 3 hours, again, the same amount of trifluoroacetic acid was added and the mixture was 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 45 mg (55% of theory) of the target compound.

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. concentrationThe reaction mixture was then concentrated
  3. 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-ddc3e2f55b4343999463233cf81d5af9
Source dataset
uspto-grants-2014_06
Patent number
US08741834B2

Reaction notes

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