Triethylamine → HCID 50923083, compound

HRID 1798328Notes

Reaction equation

HRID 1798328 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1.[CH3:19]CN(CC)CC.C[N:27]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[N:28]1>C(Cl)Cl>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][S:32]([C:29]3[N:28]([CH3:19])[N:27]=[CH:31][CH:30]=3)(=[O:34])=[O:33])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134744661-Methyl-1H-pyrazole-3-sulfonyl chlorideHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 50923083HCID 50923083, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (200 mg, 0.8 mmol) and Et3N (0.4 ml, 4 mmol) in DCM (8 mL) was added 1-methyl-1H-pyrazole-3-sulfonyl chloride (433 mg, 2.4 mmol) slowly at −78° C. Then stirred at −78° C. to rt overnight. The resulting mixture was concentrated, chromatography on silica gel, (DCM/MeOH 9.5/0.5) to get white solid. Further purification by reverse-phase prep. HPLC to get the title compound colorless oil (64 mg). 1H NMR (400 MHz, DMSO-d6) δ 9.15 (br, 1H), 8.00 (s, 1H), 7.19 (s, 1H), 6.80 (s, 1H), 6.79 (s, 1H), 5.45 (q, 2H), 4.00 (t, 3H), 2.48 (d, 2H), 2.25 (d, 1H), 2.21 (s, 3H), 1.08 (t, 3H) ppm. MS (ESI) m/z=393.0 [M−H]−.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customchromatography on silica gel, (DCM/MeOH 9.5/0.5) to get white solid
  3. customFurther purification by reverse-phase prep

Sources & evidence

ORD record
ord-5af288373cbb42cdb9c3bf1aff57e47b
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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