Trifluoroacetic acid → HCID 90072104, compound

HRID 921267Notes

Reaction equation

HRID 921267 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][CH3:45])[C:10]=3[NH:11][C:12](=[O:39])[CH:13]([NH:15][C:16]([C@H:18]([CH2:33][CH2:34][C:35]([F:38])([F:37])[F:36])[C@H:19]([CH2:27][CH2:28][C:29]([F:32])([F:31])[F:30])[C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])[N:14]=2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][CH3:45])[C:10]=3[NH:11][C:12](=[O:39])[CH:13]([NH:15][C:16]([C@H:18]([CH2:33][CH2:34][C:35]([F:37])([F:38])[F:36])[C@H:19]([CH2:27][CH2:28][C:29]([F:32])([F:31])[F:30])[C:20]([OH:22])=[O:21])=[O:17])[N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90090537HCID 90090537, compound

Product 1

HCID 90072104HCID 90072104, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Intermediate 2A (115 mg, 0.174 mmol) in DCM (3 mL) was treated with TFA (0.668 mL, 1.737 mmol). The reaction mixture was stirred at room temperature for 2 hours and then concentrated to dryness. The crude mixture was diluted with toluene and again concentrated to dryness to afford Intermediate 2B (87 mg, 0.144 mmol, 83% yield). HPLC RT=3.695 (H2O/CH3CN with TFA, Waters Sunfire C18 2.1×30 mm 3.5 um, 4 min gradient, detection at 220 nm). MS(ES): m/z=606.1 [M+H+].

Workup

  1. concentrationconcentrated to dryness
  2. additionThe crude mixture was diluted with toluene
  3. concentrationagain concentrated to dryness

Sources & evidence

ORD record
ord-52a823d97f0d45489f1dcb5a42a5cb69
Source dataset
uspto-grants-2016_03
Patent number
US09273014B2

Reaction notes

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