Hydrochloric Acid → HCID 86596963, compound

HRID 2225285Notes

Reaction equation

HRID 2225285 reaction equation
[CH:1]([S:4]([CH2:7][C@H:8]1[C@@H:17]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][CH2:15][C:10]2(OCC[O:11]2)[CH2:9]1)(=[O:6])=[O:5])([CH3:3])[CH3:2].Cl>CC(C)=O>[CH:1]([S:4]([CH2:7][C@@H:8]1[CH2:9][C:10](=[O:11])[CH2:15][CH2:16][C@@H:17]1[NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86596961HCID 86596961, compound

Product 1

HCID 86596963HCID 86596963, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of benzyl ((7R,8S)-7-(isopropylsulfonylmethyl)-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamate (2.3 g, 5.6 mmol) in acetone (30 ml) is treated with 5 N HCl (30 ml) and heated to reflux for 2 hrs. The 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 2.0 g of benzyl (1S,2R)-2-(isopropylsulfonylmethyl)-4-oxocyclohexylcarbamate. This is used without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hrs
  3. concentrationThe The 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-16ca0d887e534bc2b388a991398a74f2
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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