Hydrochloric Acid → HCID 86722945, compound

HRID 1486149Notes

Reaction equation

HRID 1486149 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][C:6]1([CH2:21][N+:22]([O-:24])=[O:23])[CH2:11][CH2:10][CH:9]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:7]1)C.[OH-].[Na+].Cl>CO.C1COCC1>[C:17]([O:16][C:14]([NH:13][CH2:12][CH:9]1[CH2:8][CH2:7][C:6]([CH2:5][C:4]([OH:25])=[O:3])([CH2:21][N+:22]([O-:24])=[O:23])[CH2:11][CH2:10]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86722944HCID 86722944, compound

Product 1

HCID 86722945HCID 86722945, compoundYield 109.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(tert-Butoxycarbonylamino-methyl)-1-nitromethyl-cyclohexyl]-acetic acid ethyl ester (0.304 g, 0.848 mmol) in MeOH (5.0 mL) and THF (1.5 mL) was added sodium hydroxide (4.2 mL, 1N, 4.2 mmol) and the reaction stirred at RT for 5 hr. The reaction was acidified to pH ˜2 with 1N HCl and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated to provide 0.308 g of crude product that was carried to the next step without purification. ESI-MS m/z 331 (MH)+.

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-352dfce204f14121a518411344e8a82e
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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