Trifluoroacetic acid → HCID 86713394, compound

HRID 921274Notes

Reaction equation

HRID 921274 reaction equation
[F:1][C:2]([F:45])([F:44])[CH2:3][CH2:4][C@@H:5]([C:20](=[O:43])[NH:21][CH:22]1[C:28](=[O:29])[NH:27][C:26]2[C:30]([CH2:34][OH:35])=[CH:31][CH:32]=[CH:33][C:25]=2[C:24]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=2)=[N:23]1)[C@H:6]([CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17])[C:7]([O:9]C(C)(C)C)=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:45][C:2]([F:1])([F:44])[CH2:3][CH2:4][C@@H:5]([C:20](=[O:43])[NH:21][CH:22]1[C:28](=[O:29])[NH:27][C:26]2[C:30]([CH2:34][OH:35])=[CH:31][CH:32]=[CH:33][C:25]=2[C:24]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=2)=[N:23]1)[C@H:6]([CH2:14][CH2:15][C:16]([F:17])([F:18])[F:19])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86713395HCID 86713395, compound

Product 1

HCID 86713394HCID 86713394, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 37I (65 mg, 0.100 mmol) in DCM (2 mL) was added TFA (2 mL). The mixture was stirred at room temperature for 3 h and then concentrated to dryness. The crude material was purified by preparative reversed-phase HPLC (aq. MeOH, containing 0.1% TFA). The desired fractions were combined and concentrated to dryness to afford Intermediate 37J (30 mg, 51%). HPLC: RT=2.680 min (CHROMOLITH® SpeedROD column 4 6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm), MS(ES): m/z=592.3 [M+H+].

Workup

  1. concentrationconcentrated to dryness
  2. customThe crude material was purified by preparative reversed-phase HPLC (aq. MeOH, containing 0.1% TFA)
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6897353858b340309ab46d42e2b6fcb0
Source dataset
uspto-grants-2016_03
Patent number
US09273014B2

Reaction notes

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