Hydrochloric Acid → HCID 57968862, compound

HRID 1483654Notes

Reaction equation

HRID 1483654 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([B:18]3[O:22][C:21](C)(C)C(C)(C)[O:19]3)=[C:14](CO)[CH:13]=2)=[CH:7][C:6]=1[O:29][CH3:30])[CH3:2].Cl.C1(B(O)O)C=CC=CC=1>CO>[CH2:1]([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]3[B:18]([OH:19])[O:22][CH2:21][C:14]=3[CH:13]=2)=[CH:7][C:6]=1[O:29][CH3:30])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66827Phenylboronic AcidHCID 57969096HCID 57969096, compound

Product 1

HCID 57968862HCID 57968862, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 9 (2.0 g, 4.67 mmol) in methanol (50 mL) was added 6N HCl (10 mL) and phenylboronic acid (2.85 g, 23.36 mmol). The resulting mixture was stirred at rt O/N. The solvent was removed under reduced pressure to give crude product, which was purified by reverse phase prep HPLC using CH3CN/H2O (with 0.1% acetic acid) as the eluent to afford the title compound (D35) (0.66 g, 39%) as a white solid after lyophilization. Mp 64.9-65.2° C. 1H NMR 400 MHz (DMSO-d6) δ: 9.20 (s, 1H), 7.80 (d, J=8.2 Hz, 1H), 7.72 (d, J=8.6 Hz, 1H), 7.18 (s, 1H), 7.16 (dd, J=8.2, 2.0 Hz, 1H), 6.80 (s, 1H), 6.60 (dd, J=8.6, 2.3 Hz, 1H), 4.98 (s, 2H), 4.21 (q, J=7.0 Hz, 2H), 3.81 (s, 3H), 1.20 (t, J=7.0 Hz, 3H); MS (ES) m/z: 329 (M+1)+; HPLC purity: 99.46% (220 nm), 100% (254 nm).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give crude product, which
  3. customwas purified by reverse phase prep HPLC

Sources & evidence

ORD record
ord-18996b23a1a44c6684d56534e963af61
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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