Trifluoroacetic acid → HCID 46853342, compound

HRID 1621337Notes

Reaction equation

HRID 1621337 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]([NH:13][C@H:14]([C:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[C:33]([C:34]#[N:35])=[C:32]([S:36][CH2:37][C:38]3[N:39]=[C:40]([C:43]4[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=4)[S:41][CH:42]=3)[N:31]=[C:30]([N:50]3[CH2:53][CH2:52][CH2:51]3)[C:29]=2[C:54]#[N:55])=[CH:24][CH:23]=1)=[O:17])[CH3:15])=[O:12])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH2:9][CH2:10][C:11]([NH:13][C@H:14]([C:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[C:33]([C:34]#[N:35])=[C:32]([S:36][CH2:37][C:38]3[N:39]=[C:40]([C:43]4[CH:44]=[CH:45][C:46]([Cl:49])=[CH:47][CH:48]=4)[S:41][CH:42]=3)[N:31]=[C:30]([N:50]3[CH2:51][CH2:52][CH2:53]3)[C:29]=2[C:54]#[N:55])=[CH:26][CH:27]=1)=[O:17])[CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59435638HCID 59435638, compound

Product 1

HCID 46853342HCID 46853342, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

90 mg (0.113 mmol) of 2-{4-(2-(azetidin-1-yl)-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyanopyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-beta-alanyl-L-alaninate (Example 4A) were initially charged in 3.5 ml of dichloromethane. 0.347 ml (4.502 mmol) of trifluoroacetic acid was added, and the reaction solution was then stirred at RT overnight. The reaction solution was concentrated by evaporation and the residue was purified by preparative HPLC (acetonitrile/water+0.1% TFA). For further purification, the product was once more purified by preparative HPLC (column material: XBridge; mobile phase: acetonitrile/0.1% aq. ammonia=65/35). This gave 51 mg (65% of theory) of the target compound.

Workup

  1. concentrationThe reaction solution was concentrated by evaporation
  2. customthe residue was purified by preparative HPLC (acetonitrile/water+0.1% TFA)
  3. customFor further purification
  4. customthe product was once more purified by preparative HPLC (column material: XBridge; mobile phase: acetonitrile/0.1% aq. ammonia=65/35)

Sources & evidence

ORD record
ord-db937c58c8fc405bbd2a0317c9b4eb95
Source dataset
uspto-grants-2014_07
Patent number
US08772498B2

Reaction notes

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