Trifluoroacetic acid → HCID 42625468, compound

HRID 1174199Notes

Reaction equation

[OH:1][C:2]([C:5]1[N:10]=[C:9]([CH2:11][N:12]2[CH2:16][CH2:15][N:14]([C@@H:17]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:18]([O:20]C(C)(C)C)=[O:19])[C:13]2=[O:29])[CH:8]=[CH:7][CH:6]=1)([CH3:4])[CH3:3].FC(F)(F)C(O)=O>O>[OH:1][C:2]([C:5]1[N:10]=[C:9]([CH2:11][N:12]2[CH2:16][CH2:15][N:14]([C@@H:17]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:18]([OH:20])=[O:19])[C:13]2=[O:29])[CH:8]=[CH:7][CH:6]=1)([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

The product of Example 50-5 (61 g, 150.6 mmol) at 25° C. was treated with 90% trifluoroacetic acid in water (300 mL). The reaction was stirred at 25° C. for 5 hours and concentrated to give 118 g of residue. The residue was loaded on 600 g of silica gel, eluted with 4 L of 5% methanol in dichloromethane, then with 4 L of 10% methanol in dichloromethane. The desired fractions were combined and concentrated to give 100 g of crude material. The crude material was crystallized from diethyl ether (350 mL) to afford 54 g of the trifluoroacetic acid salt of the title compound, 77% yield. 1H NMR (CDCl3): δ ppm 1.10 (s, 9 H,) 1.63 (s, 6 H), 3.48 (m, 2 H), 3.65 (m, 1 H), 3.87 (m, 1H), 4.33 (s, 1 H), 4.78 (q, 2 H), 7.54 (d, 1 H), 7.61 (d, 1 H), 8.12 (t, 1 H), 9.2(w, 3H).

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-432525d83b514ef4bf8e4eda071f6dac
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834043B2

Reaction notes

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