Boron Trichloride → HCID 76903418, compound

HRID 576597Notes

Reaction equation

C([O:5][C:6]([C:8]1[C:9](OC)=[C:10]([CH2:14][C@H:15]([NH:29][C:30]([C:32]2([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]2)=[O:31])[B:16]2[O:24]C3C(C)(C4CC(C3)C4(C)C)[O:17]2)[CH:11]=[CH:12][CH:13]=1)=[O:7])(C)(C)C.B(Cl)(Cl)Cl>C(Cl)Cl>[OH:24][B:16]1[C@@H:15]([NH:29][C:30]([C:32]2([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH2:33][CH2:34][NH:35][CH2:36][CH2:37]2)=[O:31])[CH2:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([C:6]([OH:5])=[O:7])[C:9]=2[O:17]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the product from step 1 (460 mg, 0.64 mmol) in anhydrous CH2Cl2 (15 mL) at −78° C. was added BCl3 (5.0 mL, 1M in DCM, 5.0 mmol), and the reaction mixture was stirred at same temperature for 1 hr, at which time the reaction mixture was warmed up to 0° C. and stirred at same temperature for additional 1 hr. The reaction was quenched by addition of water (5 mL) at 0° C. After the phase separation, the product in aqueous phase was purified by reverse phase preparative HPLC [Phenomenex Luna, 5 μm, 30×75 mm, 5-100% AcCN:H2O (with 0.1% TFA)] and dried using lyophilization to afford the product (10 mg) as while solid. ESI-MS m/z 395 (MH)+.

Workup

stirringstirred at same temperature for additional 1 hr
customThe reaction was quenched by addition of water (5 mL) at 0° C
customAfter the phase separation
customthe product in aqueous phase was purified by reverse phase preparative HPLC [Phenomenex Luna, 5 μm, 30×75 mm, 5-100% AcCN:H2O (with 0.1% TFA)]
customdried

Sources & evidence

ORD record: ord-bf5699c3d94640f4940519819afea57f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040504B2

Reaction notes

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