Hydrochloric Acid → HCID 67361944, compound

HRID 1804768Notes

Reaction equation

HRID 1804768 reaction equation
C(OC([N:8]1[C@H:13]2[CH2:14][CH2:15][C@:10]([CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][C@H:21]([O:24]C(=O)C(C)(C)C)[C@@H:20]([CH3:31])[CH2:19]3)([CH:11]=[CH:12]2)[O:9]1)=O)(C)(C)C.[ClH:32]>O>[ClH:32].[CH3:31][C@@H:20]1[C@@H:21]([OH:24])[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][C:10]23[CH2:15][CH2:14][CH:13]([CH2:12][CH2:11]2)[NH:8][O:9]3)[CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67361684(1S,4S)-1-{2-[(3S,4S)-4-(2,2-Dimethyl-propionyloxy)-3-methyl-piperidin-1-yl]-ethyl}-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid tert-butyl ester

Product 1

HCID 67361944HCID 67361944, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

(1S,4S)-1-{2-[(3S,4S)-4-(2,2-Dimethyl-propionyloxy)-3-methyl-piperidin-1-yl]-ethyl}-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid tert-butyl ester (12) (880 mg, 2 mmol) is dissolved in 20 ml of water and after addition of concentrated aqueous HCl (38%, 1.2 ml) the mixture is stirred for 16 h at 100° C. Then the mixture is evaporated to dryness. The residue s treated three times with methanol and evaporated under educed pressure. The residue is diluted with ethyl acetate, extracted with 2M K2CO3, dried over Na2SO4 and evaporated under reduced pressure. The product was used in the next step without further purification.

Workup

  1. customThen the mixture is evaporated to dryness
  2. additionThe residue s treated three times with methanol
  3. customevaporated under educed pressure
  4. additionThe residue is diluted with ethyl acetate
  5. extractionextracted with 2M K2CO3
  6. dry with materialdried over Na2SO4
  7. customevaporated under reduced pressure
  8. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-4a62558cd65e43f78387f896ed626f49
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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