Hydrochloric Acid → 1-[2-(3,8-Diazaspiro[5.5]undecan-3-yl)-2-oxo-ethyl]-3-isobutyl-urea

HRID 2284531Notes

Reaction equation

HRID 2284531 reaction equation
[CH2:1]([NH:5][C:6]([NH:8][CH2:9][C:10]([N:12]1[CH2:29][CH2:28][C:15]2([CH2:20][CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]2)[CH2:14][CH2:13]1)=[O:11])=[O:7])[CH:2]([CH3:4])[CH3:3].Cl>O1CCOCC1>[CH2:20]1[C:15]2([CH2:28][CH2:29][N:12]([C:10](=[O:11])[CH2:9][NH:8][C:6]([NH:5][CH2:1][CH:2]([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:14]2)[CH2:16][NH:17][CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118022279Tert-butyl 9-[2-(isobutylcarbamoylamino)acetyl]-4,9-diazaspiro[5.5]-undecane-4-carboxylate

Product 1

HCID 1180213681-[2-(3,8-Diazaspiro[5.5]undecan-3-yl)-2-oxo-ethyl]-3-isobutyl-ureaYield 87.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 9-[2-(isobutylcarbamoylamino)acetyl]-4,9-diazaspiro[5.5]undecane-4-carboxylate (0.38 g, 0.93 mmol) in 1,4-dioxane (1.75 mL), add 4M HCl in 1,4-dioxane (8.77 mmol). Stir the reaction at room temperature for 5 hours, then concentrate under reduced pressure. Purify the residue by dissolving in methanol and loading into a SCX (ion exchange) column. Rinse the loaded column with methanol (3×25 mL) then flush the column with 2N ammonia in methanol. Combine and concentrate the ammonia washes to yield the final title compound, 1-[2-(4,9-diazaspiro[5.5]undecan-9-yl)-2-oxo-ethyl]-3-isobutyl-urea (0.25 g, 0.81 mmol): MS (m/z): 311.0 (M+H).

Workup

  1. customthe reaction at room temperature for 5 hours
  2. concentrationconcentrate under reduced pressure
  3. customPurify the residue
  4. dissolutionby dissolving in methanol
  5. washRinse the loaded column with methanol (3×25 mL)
  6. customthen flush the column with 2N ammonia in methanol
  7. concentrationCombine and concentrate the ammonia

Sources & evidence

ORD record
ord-e4d4b53bb2e94e6a8ab71cd97593c8d1
Source dataset
uspto-grants-2015_09
Patent number
US09145435B2

Reaction notes

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