Trifluoroacetic acid → HCID 178511639, compound

HRID 1943400Notes

Reaction equation

HRID 1943400 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:27][CH:28]3[CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]3)[C:12]3[N:13]([C:15]([C:18](=[O:26])[NH:19][C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:27][CH:28]3[CH2:31][NH:30][CH2:29]3)[C:12]3[N:13]([C:15]([C:18]([NH:19][C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)=[O:26])=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452247HCID 178452247, compound

Product 1

HCID 178511639HCID 178511639, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2A (4.0 mg, 0.008 mmol) in CH2Cl2 (1 mL) was treated with TFA (0.1 mL) and stirred at room temperature for five hours. The resulting solution was concentrated and the crude product was purified by reversed-phase preparative HPLC ((YMC ODS-A 5 um 20×100 mm, 10% to 90% MeOH/H2) containing 0.1% TFA, 30 minute gradient, 20 mL/min) to afford the title compound (2.0 mg, 61%). LC/MS, m/z 422.27 (M+1). HPLC Rt=1.405 min. YMC S5 ODS-A column (4.6×50 mm) 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.2% H3PO4). Solvent A: (10% MeOH, 90% H2O, 0.2% H3PO4). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% 1 min, flow rate 4 mL/min.

Workup

  1. concentrationThe resulting solution was concentrated
  2. customthe crude product was purified by reversed-phase preparative HPLC ((YMC ODS-A 5 um 20×100 mm, 10% to 90% MeOH/H2) containing 0.1% TFA, 30 minute gradient, 20 mL/min)

Sources & evidence

ORD record
ord-4c4afdfe4eb84053bbf70d7037c7dc69
Source dataset
uspto-grants-2013_03
Patent number
US08389527B2

Reaction notes

Loading…