Trifluoroacetic acid → HCID 88545532, compound

HRID 403023Notes

Reaction equation

HRID 403023 reaction equation
C(OC([NH:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17][C@@H:18]([CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[C:50]([C:51]#[N:52])=[C:49]([S:53][CH2:54][C:55]3[N:56]=[C:57]([C:60]4[CH:65]=[CH:64][C:63]([Cl:66])=[CH:62][CH:61]=4)[O:58][CH:59]=3)[N:48]=[C:47]([NH2:67])[C:46]=2[C:68]#[N:69])=[CH:41][CH:40]=1)[CH2:19][O:20][C:21](=[O:36])[CH2:22][CH2:23][NH:24][C:25](=[O:35])[CH2:26][NH:27]C(=O)OC(C)(C)C)=[O:16])=[O:11])=O)(C)(C)C.[F:70][C:71]([F:76])([F:75])[C:72]([OH:74])=[O:73]>ClCCl>[F:70][C:71]([F:76])([F:75])[C:72]([OH:74])=[O:73].[F:70][C:71]([F:76])([F:75])[C:72]([OH:74])=[O:73].[NH2:27][CH2:26][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])[CH2:9][NH2:8])[CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[C:50]([C:51]#[N:52])=[C:49]([S:53][CH2:54][C:55]3[N:56]=[C:57]([C:60]4[CH:61]=[CH:62][C:63]([Cl:66])=[CH:64][CH:65]=4)[O:58][CH:59]=3)[N:48]=[C:47]([NH2:67])[C:46]=2[C:68]#[N:69])=[CH:41][CH:40]=1)=[O:36])=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 88545515HCID 88545515, compound

Product 1

HCID 88545532HCID 88545532, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An amount of 79 mg (0.080 mmol) of the compound from example 32A was introduced in 0.5 ml of dichloromethane, admixed with 0.061 ml (0.798 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 54 mg (65% 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-ac387d9674fd479fb088e99c6573d574
Source dataset
uspto-grants-2014_06
Patent number
US08741834B2

Reaction notes

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