Hydrochloric Acid → HCID 90313147, compound

HRID 1481284Notes

Reaction equation

HRID 1481284 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1[CH:18]=[C:17]([C:19]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([O:32][CH3:33])=[O:31])=[CH:25][C:20]=2[C:21]([O:23]C)=[O:22])[CH:16]=[CH:15][N:14]=1)[CH2:10][CH:11]=[CH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1[CH:18]=[C:17]([C:19]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([O:32][CH3:33])=[O:31])=[CH:25][C:20]=2[C:21]([OH:23])=[O:22])[CH:16]=[CH:15][N:14]=1)[CH2:10][CH:11]=[CH2:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131736621HCID 131736621, compound

Product 1

HCID 90313147HCID 90313147, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 24C (0.304 g, 0.667 mmol) in MeOH (6.67 ml) was added 1N NaOH (2.67 ml, 2.67 mmol). The reaction was stirred at rt. After 48 h, the reaction was neutralized with 1N HCl and then it was concentrated to remove the MeOH. The residue was extracted with EtOAc (2×). The organic layers were combined and washed with brine, dried over Na2SO4, filtered, and concentrated to afford 24D (0.291 g, 99%) as a yellow solid. MS (ESI) m/z: 442.2 (M+H)+.

Workup

  1. concentrationit was concentrated
  2. customto remove the MeOH
  3. extractionThe residue was extracted with EtOAc (2×)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-610893b880ca402193987c825277b144
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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