Hydrochloric Acid → HCID 58495541, compound

HRID 1190980Notes

Reaction equation

HRID 1190980 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:12][N:11]=1)=O)(C)(C)C.Cl>CO>[NH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58495605HCID 58495605, compound

Product 1

HCID 58495541HCID 58495541, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 2-(tert-butoxycarbonylamino-methyl)-5-cycloheptyloxy-pyridine (1.9 g, 5.95 mmol) in methanol (25 mL) and cool to 0° C. Bubble hydrogen chloride through the vigorously stirred solution for 30 min. Evaporate in vacuo and partition the residue between 3N aqueous NaOH (10 mL) and DCM (20 mL). Separate the two layers and extract the aqueous layer with DCM (2×20 mL). Wash the combined organic extracts with brine (20 mL), dry over Na2SO4, filter, and concentrate in vacuo to obtain the title compound as a colorless oil (941 mg, 72%). MS (APCI+) m/z: 221 (M+H)+.

Workup

  1. customEvaporate in vacuo
  2. custompartition the residue between 3N aqueous NaOH (10 mL) and DCM (20 mL)
  3. customSeparate the two layers
  4. extractionextract the aqueous layer with DCM (2×20 mL)
  5. washWash the combined organic extracts with brine (20 mL)
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-9aa1e18b15924a36941603b89f9fa8d1
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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