Methanol → HCID 131726596, compound

HRID 915886Notes

Reaction equation

ClC1C=C(Cl)C=CC=1C[O:10][C@@H:11]1[C@@H:15]([CH2:16][O:17]CC2C=CC(Cl)=CC=2Cl)[O:14][C@@H:13]([N:27]2[CH:39]=[C:31]3[CH:32]=[CH:33][C:34]4[CH2:35][NH:36][N:37]=[CH:38][C:29]([C:30]=43)=[N:28]2)[C@:12]1([CH3:41])[OH:40].B(Cl)(Cl)Cl.CO>C(Cl)Cl>[CH3:41][C@@:12]1([OH:40])[C@H:11]([OH:10])[C@@H:15]([CH2:16][OH:17])[O:14][C@H:13]1[N:27]1[CH:39]=[C:31]2[CH:32]=[CH:33][C:34]3[CH2:35][NH:36][N:37]=[CH:38][C:29]([C:30]=32)=[N:28]1

Participants

Conditions

Temperature: -78 °C

Procedure

To compound 24.1 (160 mg, 0.25 mmol) in CH2Cl2 (10 mL) at −78° C. was added 1M solution of boron trichloride in CH2Cl2 dropwise over 5 minutes and the solution stirred at −78° C. for 2.5 h and then at −25° C. for 3 hr. To this mixture was added 25 mL of 1:1 v/v CH2Cl2:MeOH and the solution stirred at −15° C. for 30 minutes. The mixture was brought to room temperature and the solvent was evaporated under reduced pressure. The residue was co-evaporated with MeOH (5×10 mL) and a 10 mL MeOH solution was neutralized with NH4OH and evaporated again. The residue was adsorbed on 2 g silica gel and loaded on a silica column and eluted successively with 50:1,20:1 and 15:1 CH2Cl2:MeOH. Fractions eluting at 20:1 and 15:1 were collected, Pooling of fraction and evaporation gave 16 mg product 24.2. 1H NMR (DMSO-d6) δ 8.10 (s, 1H), 7.51 (s, 1H), 7.30 (t, 1H), 6.61 (d, J 9 Hz, 1H), 6.11 (s, 1H), 5.71 (dt, J 6, 12 Hz, 1H), 5.08 (m, 3H), 3.86 (m, 5H), 3.78 (m, 1H), 0.72 (s, 31).

Workup

waitat −25° C. for 3 hr
customwas brought to room temperature
customthe solvent was evaporated under reduced pressure
customevaporated again
washeluted successively with 50:1,20:1 and 15:1 CH2Cl2
washFractions eluting at 20:1 and 15:1
customwere collected
customPooling of fraction and evaporation

Sources & evidence

ORD record: ord-7d0654f3bfaa47e0b7f68f71c2c203ec
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268119B2

Reaction notes

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