Hydrochloric Acid → Hydrochloric Acid

HRID 732604Notes

Reaction equation

HRID 732604 reaction equation
C(OC([N:8]1[CH:13]([CH:14]([OH:27])[CH:15]([NH:23][C:24](=[O:26])[CH3:25])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]2[CH:28]([CH2:29][O:30][CH3:31])[CH:9]1[CH2:10][CH2:11]2)=O)(C)(C)C.[ClH:32]>O1CCCC1>[ClH:32].[CH2:16]([CH:15]([NH:23][C:24](=[O:26])[CH3:25])[CH:14]([OH:27])[CH:13]1[CH:12]2[CH:28]([CH2:29][O:30][CH3:31])[CH:9]([CH2:10][CH2:11]2)[NH:8]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1.[ClH:32]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68814412HCID 68814412, compound

Product 2

HCID 313Hydrochloric AcidHCID 68814491HCID 68814491, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cool a solution of 3-(2-acetylamino-1-hydroxy-3-phenylpropyl)-7-methoxymethyl-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (Isomer 1) (0.044 g, 0.102 mmol) in tetrahydrofuran (1 mL) and add a solution of hydrochloric acid (2.0 mL, 4 M in 1,4-dioxane). Stir the mixture for 5 h at room temperature, concentrate and purify (silica gel chromatography, eluting with 2 M ammonia in 5:95 to 10:90 methanol:dichloromethane) to give the title compound after treatment with the same equivalent of hydrochloric acid in diethyl ether (16 mg, 43%).

Workup

  1. concentrationconcentrate
  2. custompurify
  3. wash(silica gel chromatography, eluting with 2 M ammonia in 5:95 to 10:90 methanol:dichloromethane)

Sources & evidence

ORD record
ord-53e81a6dec87437b8ed84f92166e834d
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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