Sodium Carbonate → HCID 118308191, compound

HRID 1750556Notes

Reaction equation

HRID 1750556 reaction equation
[CH3:1][C:2]([S:5]([NH:8][CH:9]1[CH:17]([NH:18][C@@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])[CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10]1)(=[O:7])=[O:6])([CH3:4])[CH3:3].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35]>O1CCOCC1.O>[CH3:1][C:2]([S:5]([NH:8][CH:9]1[CH2:10][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:16][CH:17]1[N:18]([C@@H:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:20])[C:34](=[O:35])[O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:6])=[O:7])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 118308271HCID 118308271, compound

Product 1

HCID 118308191HCID 118308191, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-methyl-N-(8-{[(1R)-1-phenylethyl]amino}-1,4-dioxaspiro[4.4]nonan-7-yl)propane-2-sulfonamide (274 mg, 0.72 mmol) and sodium carbonate (114 mg, 1.074 mmol) in 1,4-dioxane (2 ml) and water (0.4 ml) at 0° C. was added drop wise benzyl chloroformate (CAS number 501-53-1; 0.13 ml, 0.90 mmol). The reaction mixture was allowed to warm to room temperature for 2 hours then concentrated in vacuo. The residue was diluted with ethyl acetate and washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography (silica, 0-70% ethyl acetate/petrol) to afford the title compound.

Workup

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by column chromatography (silica, 0-70% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-9b84f64f15234d048b68d50bcf11ac33
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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