Trifluoroacetic acid → HCID 90087881, compound

HRID 593488Notes

Reaction equation

HRID 593488 reaction equation
[F:1][C:2]([F:44])([F:43])[CH2:3][CH2:4][C@@H:5]([C:20](=[O:42])[NH:21][CH:22]1[C:28](=[O:29])[NH:27][C:26]2[CH:30]=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:25]=2[C:24]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][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].FC(F)(F)C(O)=O>C(Cl)Cl>[F:44][C:2]([F:1])([F:43])[CH2:3][CH2:4][C@@H:5]([C:20](=[O:42])[NH:21][CH:22]1[C:28](=[O:29])[NH:27][C:26]2[CH:30]=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:25]=2[C:24]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[N:23]1)[C@H:6]([CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118345109HCID 118345109, compound

Product 1

HCID 90087881HCID 90087881, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of Intermediate 7D (1.03 mg, 0.836 mmol) in CH2Cl2 (8 mL) at 0° C. under a nitrogen atmosphere, was added trifluoroacetic acid (3 mL) dropwise over two minutes. The reaction mixture was stirred at 0° C. for one hour and then stirred at room temperature for five hours. The reaction mixture was then concentrated and treated with ice cold water (50 grams). After stirring for fifteen minutes, the off-white precipitate was filtered, washed with water (5 mL) and dried to provide Intermediate 7E as a white solid: yield=500 mg (84%); HPLC: RT=2.282 (H2O/AcCN with NH4OAc, PUROSPHER® Star RP-18 (4×55) mm, 3 μm, gradient=3 min, wavelength=220 nm); MS(ES):m/z=572 [M−H+]; 1H NMR (DMSO-d6: as mixture of diastereomers) δ 10.67 (s, 1H), 9.51-9.54 (t, J=7.2 Hz, 1H), 7.5-7.6 (m, 3H), 7.5 (m, 2H), 7.1-7.3 (m, 4H), 6.771 (s, 1H), 5.29 (t, J=8.0 Hz, 1H), 3.7 (s, 3H), 2.80-2.91 (m, 1H), 2.70 (m, 1H), 2.50 (m, 1H), 2.10-2.34 (m, 3H), 1.50-1.90 (m, 3H).

Workup

  1. stirringstirred at room temperature for five hours
  2. concentrationThe reaction mixture was then concentrated
  3. additiontreated with ice cold water (50 grams)
  4. stirringAfter stirring for fifteen minutes
  5. filtrationthe off-white precipitate was filtered
  6. washwashed with water (5 mL)
  7. customdried

Sources & evidence

ORD record
ord-b374337cb0e244a18a1e82eff62dc45c
Source dataset
uspto-grants-2016_01
Patent number
US09242940B2

Reaction notes

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