Boron Trichloride → HCID 178429247, compound

HRID 734755Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[CH:19]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([O:27]C)[CH:21]=4)[CH2:18][C:17](=[O:29])[NH:16][C:15]=3[CH3:30])=[O:13])[CH:9]=2)[NH:4][N:3]=1.B(Cl)(Cl)Cl>C(Cl)Cl.CCOC(C)=O.O.[OH-].[Na+]>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH:19]2[CH2:18][C:17](=[O:29])[NH:16][C:15]([CH3:30])=[C:14]2[C:12]([NH:11][C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[Cl:1])=[O:13])=[CH:21][C:22]=1[OH:27]

Participants

Conditions

Temperature: 35 °C

Procedure

The product of Example 93, Step 5 (75 mg, 0.168 mmol, 1.0 equiv) was cooled to −78° C. in 1.75 mL CH2Cl2 and BCl3 (1.0 M in CH2Cl2, 2.5 mL, 2.526 mmol, 15.0 equiv) was added dropwise. The reaction was warmed to 35° C. and stirred for 90 hours. An additional portion of BCl3 (2.5 mL, 2.526 mmol, 15.0 equiv) in CH2Cl2 was added dropwise and the reaction was stirred for another 96 hours. The reaction mixture was diluted with EtOAc and water and basified to pH 14 with 6N NaOH. The phases were separated, and the aqueous phase was acidified to pH 4 with 6N HCl. The precipitate was filtered and washed with Et2O. The residue was purified by reverse-phase HPLC (10-90% CH3CN/H2O, 0.1% TFA over 18 minutes, retention time 10.55 min) to provide 16 mg (22%) of the title compound as a white solid. MS (ES+) m/e 432 [M+H]+

Workup

stirringthe reaction was stirred for another 96 hours
customThe phases were separated
filtrationThe precipitate was filtered
washwashed with Et2O
customThe residue was purified by reverse-phase HPLC (10-90% CH3CN/H2O, 0.1% TFA over 18 minutes, retention time 10.55 min)

Sources & evidence

ORD record: ord-dc8dc83ad8074841962d422166b43b78
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592357B2

Reaction notes

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