Trifluoroacetic acid → HCID 86659579, compound

HRID 403021Notes

Reaction equation

HRID 403021 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:71]=[CH:70][C:13]([O:14][CH2:15][C@@H:16]([CH2:43][O:44][C:45](=[O:69])[C@H:46]([CH3:68])[NH:47][C:48](=[O:67])[CH2:49][CH2:50][C@H:51]([NH:59]C(OC(C)(C)C)=O)[C:52]([O:54]C(C)(C)C)=[O:53])[O:17][C:18](=[O:42])[C@H:19]([CH3:41])[NH:20][C:21](=[O:40])[CH2:22][CH2:23][C@H:24]([NH:32]C(OC(C)(C)C)=O)[C:25]([O:27]C(C)(C)C)=[O:26])=[CH:12][CH:11]=2)[C:5]([C:72]#[N:73])=[C:4]([S:74][CH2:75][C:76]2[N:77]=[C:78]([C:81]3[CH:86]=[CH:85][C:84]([Cl:87])=[CH:83][CH:82]=3)[O:79][CH:80]=2)[N:3]=1.[F:88][C:89]([F:94])([F:93])[C:90]([OH:92])=[O:91]>ClCCl>[F:88][C:89]([F:94])([F:93])[C:90]([OH:92])=[O:91].[F:88][C:89]([F:94])([F:93])[C:90]([OH:92])=[O:91].[NH2:32][C@@H:24]([CH2:23][CH2:22][C:21](=[O:40])[NH:20][C@@H:19]([CH3:41])[C:18](=[O:42])[O:17][C@@H:16]([CH2:15][O:14][C:13]1[CH:12]=[CH:11][C:10]([C:6]2[C:5]([C:72]#[N:73])=[C:4]([S:74][CH2:75][C:76]3[N:77]=[C:78]([C:81]4[CH:82]=[CH:83][C:84]([Cl:87])=[CH:85][CH:86]=4)[O:79][CH:80]=3)[N:3]=[C:2]([NH2:1])[C:7]=2[C:8]#[N:9])=[CH:71][CH:70]=1)[CH2:43][O:44][C:45](=[O:69])[C@H:46]([CH3:68])[NH:47][C:48](=[O:67])[CH2:49][CH2:50][C@H:51]([NH2:59])[C:52]([OH:54])=[O:53])[C:25]([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86659581HCID 86659581, compound

Product 1

HCID 86659579HCID 86659579, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An amount of 120 mg (0.096 mmol) of the compound from example 27A was introduced in 1 ml of dichloromethane, admixed with 0.074 ml (0962 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 20 mg (18% 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-c3833e1a181447ad8851b1625e0ae5a7
Source dataset
uspto-grants-2014_06
Patent number
US08741834B2

Reaction notes

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