HCID 178497643, compound → HCID 178458101, compound

HRID 878794Notes

Reaction equation

HRID 878794 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([S:21](=[O:27])(=[O:26])[NH:22][CH:23]([CH3:25])[CH3:24])[CH:19]=2)[NH:14][C:13]1=[O:28]>CO.[OH-].[Na+]>[CH:23]([NH:22][S:21]([C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:28])[C:12]2=[CH:11][NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:29])=[O:2])(=[O:27])=[O:26])([CH3:25])[CH3:24]

Participants

4

Reactant 1

HCID 178497643HCID 178497643, compound

Product 1

HCID 178458101HCID 178458101, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of rpm335 (0.155 g, 0.3734 mmol) in methanol (1 mL) and NaOH 1M (1 ml) was heated in the microwave at 150° C. for 5 min. The reaction mixture was cooled to 0° C., and the solvent distilled under reduced pressure and HCl (aq 4M, 5 ml) added. The orange precipitate was collected by filtration, washed with water (10 ml) and dried, to give pure rpm336 (0.139 g, 0.346 mmol, 92%). MS (API-ES): m/z 402 (M+H)+; HRMS (API-ES) m/z Found: 402.1116 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. distillationthe solvent distilled under reduced pressure and HCl (aq 4M, 5 ml)
  3. additionadded
  4. filtrationThe orange precipitate was collected by filtration
  5. washwashed with water (10 ml)
  6. customdried
  7. customto give pure rpm336 (0.139 g, 0.346 mmol, 92%)

Sources & evidence

ORD record
ord-f7c1eb3cad3b475292276b5dfe8447c0
Source dataset
uspto-grants-2015_03
Patent number
US08987474B2

Reaction notes

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