Hydrochloric Acid → HCID 66799079, compound

HRID 1193312Notes

Reaction equation

HRID 1193312 reaction equation
Cl.[CH3:2][C:3]1([CH3:24])[CH:12]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][CH2:10][C:5]2(OCC[O:6]2)[CH2:4]1>CO>[CH3:2][C:3]1([CH3:24])[CH2:4][C:5](=[O:6])[CH2:10][CH2:11][CH:12]1[NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66798689HCID 66798689, compound

Product 1

HCID 66799079HCID 66799079, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2 M HCl (14 ml) was added to a solution of benzyl 7,7-dimethyl-1,4-dioxaspiro[4.5]decan-8-ylcarbamate (1.4 g, 4.3887 mmol, 1 eq) in MeOH (14 ml), and stirring was carried out for 18 h at RT. The solvent was concentrated under reduced pressure and the residue was diluted with water (10 ml) and rendered basic with sat. sodium hydrogen carbonate solution (20 ml). Then extraction with ethyl acetate (2×50 ml) was carried out. The combined organic phases were washed with water (50 ml) and sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was used in the next step without being purified further. Yield: 91% (1.1 g, 4.0 mmol).

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. additionthe residue was diluted with water (10 ml)
  3. extractionThen extraction with ethyl acetate (2×50 ml)
  4. washThe combined organic phases were washed with water (50 ml) and sat. NaCl solution (50 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customwithout being purified further

Sources & evidence

ORD record
ord-2f5b3490934e4f7fb1a45737963c6e17
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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