Boron Trichloride → HCID 178438010, compound

HRID 734758Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([NH:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][N:23]=[C:22]3[CH2:28][CH3:29])=[O:17])=[CH:4][C:3]=1[O:30]C.B(Cl)(Cl)Cl>C(Cl)Cl.CCOC(C)=O.O.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([NH:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][N:23]=[C:22]3[CH2:28][CH3:29])=[O:17])=[CH:4][C:3]=1[OH:30]

Participants

Conditions

Temperature: 30 °C

Procedure

The product from Example 96 (0.050 g, 0.11 mmol, 1.0 equiv) was cooled to −78° C. in 1.5 mL CH2Cl2 and BCl3 (1.0 M in CH2C2, 1.70 mL, 1.71 mmol, 15.0 equiv) was added dropwise. The reaction was warmed to 30° C. and stirred for 72 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 and the product was extracted into EtOAc. The organic layer was washed with sat'd NaCl and concentrated en vacuo. The residue purified by reverse-phase HPLC (10-95% CH3CN/H2O, 0.1% TFA over 6 minutes, retention time 3.48 min) to provide 1 mg (0.7%) of the title compound as a white solid. MS (ES+) m/e 425 [M+H]+

Workup

customThe phases were separated
extractionthe product was extracted into EtOAc
washThe organic layer was washed with sat'd NaCl
concentrationconcentrated en vacuo
customThe residue purified by reverse-phase HPLC (10-95% CH3CN/H2O, 0.1% TFA over 6 minutes, retention time 3.48 min)

Sources & evidence

ORD record: ord-a586a7e3343144f9b3f75c55ab1a7b90
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592357B2

Reaction notes

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