Hydrochloric Acid → HCID 86680187, compound

HRID 406788Notes

Reaction equation

HRID 406788 reaction equation
C(OC(=O)[NH:7][CH2:8][C@@H:9]1[CH2:11][C@H:10]1[C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[O:19][CH2:20][CH:21]1[CH2:23][CH2:22]1)(C)(C)C.C(OCC)C.[ClH:30]>>[ClH:30].[CH:21]1([CH2:20][O:19][C:13]2[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=2[C@@H:10]2[CH2:11][C@H:9]2[CH2:8][NH2:7])[CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86680189HCID 86680189, compound

Product 1

HCID 86680187HCID 86680187, compoundYield 91.5%

Procedure

The protected amine 11 (5.8 g, 17.3 mmol) was dissolved in a 2 N HCl solution in diethyl ether (43 mL, 86 mmol), and the reaction mixture was stirred at ambient temperature for 48 h. A white precipitate formed after several hours, and the mixture was stirred until the reaction was complete by TLC. The crude precipitate was filtered and purified by recrystallization from ethanol/Et2O to afford the title compound as a white powder (4.3 g, 91.5% yield). HPLC purity: 12.0 min, 99.8%. 1H NMR (400 MHz, MeOD) δ 6.86-6.70 (m, 3 H), 3.91-3.78 (m, 2 H), 3.04 (d, J=7.2 Hz, 2 H), 2.18-2.12 (m, 1 H), 1.32-1.28 (m, 1 H), 1.16-1.02 (m, 2 H), 0.64-0.62 (m, 2 H), 0.39-0.37 (m, 2 H). 13C NMR (100 MHz, MeOD) δ 158.6 (d, 1 J CF=236.9 Hz), 155.4, 132.7 (d, 3 J CF=7.6 Hz), 114.5, 114.2, 114.2, 114.0, 114.0, 75.1, 45.2, 19.8, 18.4, 13.4, 11.4, 4.0, 3.6. MS (ESI) m/z 236.2 [MH+].

Workup

  1. customA white precipitate formed after several hours
  2. stirringthe mixture was stirred until the reaction
  3. filtrationThe crude precipitate was filtered
  4. custompurified by recrystallization from ethanol/Et2O

Sources & evidence

ORD record
ord-dbcb831c01074c34843e70719b045b9f
Source dataset
uspto-grants-2014_06
Patent number
US08754132B2

Reaction notes

Loading…