Hydrochloric Acid → HCID 57969027, compound

HRID 1471505Notes

Reaction equation

HRID 1471505 reaction equation
C([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:21]=[CH:20][C:15]3[B:16]([OH:19])[O:17][CH2:18][C:14]=3[CH:13]=2)=[CH:7][C:6]=1[O:22][CH3:23])C.[OH-].[Na+].Cl>CO.O>[OH:19][B:16]1[C:15]2[CH:20]=[CH:21][C:12]([O:11][C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:24])=[O:3])=[C:6]([O:22][CH3:23])[CH:7]=3)=[CH:13][C:14]=2[CH2:18][O:17]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57968862HCID 57968862, compound

Product 1

HCID 57969027HCID 57969027, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound (D35) (0.1 g, 0.31 mmol) in methanol (2 mL) was added 2N NaOH (1 mL). The resulting mixture was stirred at rt O/N. The solvent was removed under reduced pressure to give crude product, which was dissolved in H2O (1 mL) and acidified using 1N HCl. The solid obtained which was filtered and washed with ether (10 mL) to afford the title compound (D36) (78 mg, 86%) as a white solid. Mp 109.6-110.1° C. 1H NMR 400 MHz (DMSO-d6) δ: 9.20 (s, 1H), 7.80 (d, J=8.2 Hz, 1H), 7.75 (d, J=8.6 Hz, 1H), 7.18 (s, 1H), 7.15 (d, J=9.4 Hz, 1H), 6.80 (s, 1H), 6.60 (d, J=8.6 Hz, 1H), 4.98 (s, 2H), 3.81 (s, 3H); MS (ES) m/z: 301 (M+1)+; HPLC purity: 100% (220 nm), 99.79% (254 nm).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give crude product, which
  3. customThe solid obtained which
  4. filtrationwas filtered
  5. washwashed with ether (10 mL)

Sources & evidence

ORD record
ord-cf67abd87c7144dfac9ca73b7d15fe91
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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