Hydrochloric Acid → HCID 131735847, compound

HRID 2206312Notes

Reaction equation

HRID 2206312 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][S:11]([NH:14][CH2:15][B:16]([OH:18])[OH:17])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[OH:19][C:20]([C:23]([OH:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].[ClH:27]>C(OCC)(=O)C.[Pd]>[ClH:27].[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][S:11]([NH:14][CH2:15][B:16]([OH:18])[OH:17])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1.[OH:19][C:20]([C:23]([OH:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131735848HCID 131735848, compound

Product 1

HCID 131735847HCID 131735847, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium 10 wt. % on activated carbon (51 mg, 40% w/w) was added to a solution of 6 (128 mg, 0.36 mmol) in ethyl acetate (4 mL), and allowed to react under hydrogen atmosphere for 16 h. The catalyst was filtered off and the solvent was evaporated in vacuo. The crude residue was dissolved in HCl (0.1 M soln in MeOH, 3.6 mL, 0.36 mmol). After 45 min the mixture was concentrated under reduced pressure and the residue repeatedly washed with diethyl ether, affording 7 as a yellowish solid (118 mg, 90% yield). Mp 193-196° C. 1H-NMR (400 MHz, DMSO): δ 1.23 (12H, s, pinacol protons), 2.59 (2H, d, J 3.82, BCH2), 4.37 (2H, s, PhCH2), 6.76 (1H, br, SO2NH), 7.30-7.36 (3H, m, HArom), 7.46 (1H, t, J 7.60, HArom), 9.60-10.60 (3H, br, NH3+). 13C-NMR (100 MHz, DMSO): δ 25.0, 27.5 (CB), 55.9, 84.2, 122.8, 125.3, 130.1, 130.5, 132.7, 133.0. EI-MS, m/z: 326 (M+, 5%), 156 (8), 107 (64), 106 (100), 104 (15), 77 (11), 59 (11), 41 (8). Anal. Calcd. for C14H24BClN2O4S: C, 46.36; H, 6.67; N, 7.72; S, 8.84. Found: C, 46.41; H, 6.50; N, 7.55; S, 8.68.

Workup

  1. customto react under hydrogen atmosphere for 16 h
  2. filtrationThe catalyst was filtered off
  3. customthe solvent was evaporated in vacuo
  4. concentrationAfter 45 min the mixture was concentrated under reduced pressure
  5. washthe residue repeatedly washed with diethyl ether

Sources & evidence

ORD record
ord-63e0a50bca36414c8181d66924ed821f
Source dataset
uspto-grants-2016_06
Patent number
US09371337B2

Reaction notes

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