Boron Trichloride → HCID 60104736, compound

HRID 1836214Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[C:4]([Cl:42])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:32][C@H:31]([CH2:33][O:34]CC4C=CC=CC=4)[C@@H:22]([O:23]CC4C=CC=CC=4)[C@@H:13]3[O:14]CC3C=CC=CC=3)[C:6]=2[N:7]=1.B(Cl)(Cl)Cl>ClCCl>[NH2:1][C:2]1[N:3]=[C:4]([Cl:42])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:32][C@H:31]([CH2:33][OH:34])[C@@H:22]([OH:23])[C@@H:13]3[OH:14])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a precooled (−78° C.) solution of the compound from Step A (0.99 g, 1.7 mmol) in dichloromethane (30 mL) was added borontrichloride (1M in dichloromethane) (17 mL, 17.0 mmol) over a 10 min. The resulting solution was stirred at −78° C. for 1 h, allowed to warm to −15° C. and stirred for another 3 h. The reaction was quenched by addition of methanol/dichloromethane (1:1) (15 mL), stirred at −15° C. for 30 min, and pH adjusted to 7.0 by addition of NH4OH. The mixture was evaporated in vacuo and the resulting oil purified on silica using methanol/dichloromethane (1:9) as eluent. Fractions containing the product were pooled and evaporated in vacuo to give the desired product (257 mg) as a colorless foam.

Workup

temperatureto warm to −15° C.
stirringstirred for another 3 h
customThe reaction was quenched by addition of methanol/dichloromethane (1:1) (15 mL)
stirringstirred at −15° C. for 30 min
additionpH adjusted to 7.0 by addition of NH4OH
customThe mixture was evaporated in vacuo
customthe resulting oil purified on silica
additionFractions containing the product
customevaporated in vacuo

Sources & evidence

ORD record: ord-95c021a322f547ad8ee9c9c908c6b159
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777395B2

Reaction notes

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