Hydrochloric Acid → HCID 86596941, compound

HRID 2225234Notes

Reaction equation

HRID 2225234 reaction equation
[CH2:1]([C@@H:5]1[C@@H:14]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH2:6]1)[CH2:2][CH2:3][CH3:4].Cl>CC(C)=O>[CH2:1]([C@@H:5]1[CH2:6][C:7](=[O:8])[CH2:12][CH2:13][C@@H:14]1[NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86596940HCID 86596940, compound

Product 1

HCID 86596941HCID 86596941, compoundYield 115.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of benzyl ((7S,8S)-7-(butyl)-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamate (3 g, 0.008 mol) in acetone (30 mL) is treated with 1 N HCl (30 mL) and heated to reflux for 2 hrs. The mixture is concentrated on a rotary evaporator and the residue neutralized with 1 N NaOH and extracted into CH2Cl2. The organic extracts were washed with water, brine, and the solvent remove under vacuum to give 2.8 g of the benzyl (1S,2R)-2-butyl-4-oxocyclohexylcarbamate. This is used without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hrs
  3. concentrationThe mixture is concentrated on a rotary evaporator
  4. extractionextracted into CH2Cl2
  5. washThe organic extracts were washed with water, brine
  6. customthe solvent remove under vacuum

Sources & evidence

ORD record
ord-e2685582771b4ca58e4119cd4b7b2586
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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