Hydrochloric Acid → HCID 86596856, compound

HRID 1455377Notes

Reaction equation

HRID 1455377 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:26][CH2:25][C:20]3(OCC[O:21]3)[CH2:19][CH2:18]2)[C:13]1=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl.C(=O)(O)[O-].[Na+]>CC(C)=O>[O:27]=[C:13]1[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:16][CH2:15][N:14]1[CH:17]1[CH2:26][CH2:25][C:20](=[O:21])[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 68769760HCID 68769760, compound

Product 1

HCID 86596856HCID 86596856, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

8-((3S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-1,4-dioxaspiro[4.5]decane (2.70 g, 7.21 mmol, 1 eq.) and p-toluene sulfonic acid (0.14 g, 0.721 mmol, 0.1 eq.) were dissolved in acetone (20 mL) at room temperature. Refluxed for 4 hours. Reaction was not complete by TLC. Added 1 N HCl (10 mL). Refluxed for 10 minutes. Stripped off the acetone. Added saturated sodium bicarbonate (25 mL). Extracted 3 times with methylene chloride (25 mL). The organic layers were combined, dried over sodium sulfate and stripped to give benzyl (3S)-2-oxo-1-(4-oxocyclohexyl)-pyrrolidin-3-ylcarbamate (2.40 g) as an amber glass. Yield=95%. LCMS detects (M+)+=375.14.

Workup

  1. temperatureRefluxed for 4 hours
  2. customReaction
  3. temperatureRefluxed for 10 minutes
  4. extractionExtracted 3 times with methylene chloride (25 mL)
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-2de614cf958246f8aa5d1f7e6a095d1e
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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