Potassium Hydroxide → HCID 46908669, compound

HRID 1258396Notes

Reaction equation

HRID 1258396 reaction equation
CN(C)[C:3](=O)[S:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([N+:15]([O-:17])=[O:16])=[CH:7][CH:6]=1.[OH-].[K+].BrC[C:24]([O:26]C(C)(C)C)=[O:25]>CO>[N+:15]([C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([S:4][CH2:3][C:24]([OH:26])=[O:25])=[CH:6][CH:7]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 79177tert-Butyl bromoacetateHCID 46908668HCID 46908668, compound

Product 1

HCID 46908669HCID 46908669, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

97 mg 19 was suspended in 1 ml methanol, to which, in Argon atmosphere, was added 1.4 ml KOH solution (1M in CH3OH). The resulting mixture was stirred at room temperature for 12 hours affording a homogenous solution. 103 μl tert butyl bromoacetate was added through syringe. The reaction solution was continued for 12 hours and concentrated. The residue was dissolved in water and acidified with solid NaHSO4. The yellow precipitate was filtered and washed with water. Dried in air, 78.8 mg (85.6%, 2 steps) yellow solid was obtained. 1H NMR (400 MHz, CDCl3) δ 8.63 (d, J=8.4 Hz, 1H), 8.40 (d, J=8.4 Hz, 1H), 8.18 (d, J=8.1 Hz, 1H), 7.77 (t, J=7.6 Hz, 1H), 7.69 (t, J=7.6 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 3.91 (s, 2H). LRMS (ES−) 218 (M—H—CO2)−; HRMS (ES−) m/z calculated for C12H8NO4S (M−H)− 262.0180, found 262.0180.

Workup

  1. customaffording a homogenous solution
  2. waitThe reaction solution was continued for 12 hours
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in water
  5. filtrationThe yellow precipitate was filtered
  6. washwashed with water
  7. customDried in air, 78.8 mg (85.6%, 2 steps) yellow solid
  8. customwas obtained

Sources & evidence

ORD record
ord-e4528643bcb6470a831ca31219019347
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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