Trifluoroacetic acid → HCID 86659573, compound

HRID 403019Notes

Reaction equation

HRID 403019 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:69]=[CH:68][C:13]([O:14][CH2:15][C@@H:16]([CH2:42][O:43][C:44](=[O:67])[C@H:45]([CH3:66])[NH:46][C:47](=[O:65])[C@@H:48]([NH:57]C(OC(C)(C)C)=O)[CH2:49][C:50]([O:52]C(C)(C)C)=[O:51])[O:17][C:18](=[O:41])[C@H:19]([CH3:40])[NH:20][C:21](=[O:39])[C@@H:22]([NH:31]C(OC(C)(C)C)=O)[CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[CH:12][CH:11]=2)[C:5]([C:70]#[N:71])=[C:4]([S:72][CH2:73][C:74]2[N:75]=[C:76]([C:79]3[CH:84]=[CH:83][C:82]([Cl:85])=[CH:81][CH:80]=3)[O:77][CH:78]=2)[N:3]=1.[F:86][C:87]([F:92])([F:91])[C:88]([OH:90])=[O:89]>ClCCl>[F:86][C:87]([F:92])([F:91])[C:88]([OH:90])=[O:89].[F:86][C:87]([F:92])([F:91])[C:88]([OH:90])=[O:89].[NH2:31][C@H:22]([C:21](=[O:39])[NH:20][C@@H:19]([CH3:40])[C:18](=[O:41])[O:17][C@@H:16]([CH2:15][O:14][C:13]1[CH:12]=[CH:11][C:10]([C:6]2[C:5]([C:70]#[N:71])=[C:4]([S:72][CH2:73][C:74]3[N:75]=[C:76]([C:79]4[CH:80]=[CH:81][C:82]([Cl:85])=[CH:83][CH:84]=4)[O:77][CH:78]=3)[N:3]=[C:2]([NH2:1])[C:7]=2[C:8]#[N:9])=[CH:69][CH:68]=1)[CH2:42][O:43][C:44](=[O:67])[C@H:45]([CH3:66])[NH:46][C:47](=[O:65])[C@@H:48]([NH2:57])[CH2:49][C:50]([OH:52])=[O:51])[CH2:23][C:24]([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86659575HCID 86659575, compound

Product 1

HCID 86659573HCID 86659573, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An amount of 410 mg (0.336 mmol) of the compound from example 24A was introduced in 2 ml of dichloromethane, admixed with 0.259 ml (3.364 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 191 mg (50% 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-6b2c4b7d346e4a75871607e8c920ace9
Source dataset
uspto-grants-2014_06
Patent number
US08741834B2

Reaction notes

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