Lithium Hexamethyldisilazide → HCID 67254506, compound

HRID 1798227Notes

Reaction equation

C([O:3][C:4](=[O:26])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[N:22][C:21]([C:24]#[N:25])=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[C:24]([C:21]1[N:22]=[CH:23][C:18]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([OH:26])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[N:19][CH:20]=1)#[N:25]

Participants

Conditions

Temperature: 0 °C

Procedure

[6-(5-Cyano-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (100 mg, 0.28 mmol) was dissolved in THF (4 mL) and cooled to 0° C. To this was added LHMDS (1M in THF, 0.28 mL, 0.28 mmol) and stirred at 0° C. for 1 h. Another portion of LHMDS (1M in THF, 0.28 mL, 0.28 mmol) was added at 0° C. The reaction was stirred at 0° C. for 2 h and was allowed to warm up to room temperature. The reaction was stirred at room temperature for 6 h. The solvent was removed. Preparative HPLC (C18 column) gave the title compound (33 mg, 36%) as a white solid. MS (ESI) m/z: 326 [M+1]+; 1H NMR (300 MHz, CD3OD) δ 8.56 (1H, s), 8.50 (1H, s), 7.28 (1H, s), 7.15 (1H, s), 5.65 (1H, dd), 3.18 (1H, dd), 2.35 (3H, s), 2.30 (1H, m).

Workup

stirringThe reaction was stirred at 0° C. for 2 h
temperatureto warm up to room temperature
stirringThe reaction was stirred at room temperature for 6 h
customThe solvent was removed

Sources & evidence

ORD record: ord-510b14474886476eb7877db5ad49ef8d
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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