Acetic Anhydride → HCID 66818117, compound

HRID 1754920Notes

Reaction equation

HRID 1754920 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17]([N:20]2[CH2:36][CH2:35][C:23]3([N:27]=[C:26]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)[NH:25][C:24]3=[O:34])[CH2:22][CH2:21]2)(=[O:19])=[O:18])=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:28]1([C:26]2[NH:25][C:24](=[O:34])[C:23]3([CH2:22][CH2:21][N:20]([S:17]([CH2:16][CH2:15][C:12]4[CH:13]=[CH:14][C:9]([NH:8][C:5](=[O:7])[CH3:6])=[CH:10][CH:11]=4)(=[O:18])=[O:19])[CH2:36][CH2:35]3)[N:27]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 66816304HCID 66816304, compound

Product 1

HCID 66818117HCID 66818117, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetic anhydride (45 mg, 0.44 mmol) was added to a solution of 8-[2-(4-amino-phenyl)-ethanesulfonyl]-2-cyclohexyl-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (92 mg, 0.22 mmol) in CH2Cl2 (5 mL). Triethylamine (55 mg, 0.5 mmol) was then added on an ice bath, and the mixture was stirred at room temperature for one hour. The reaction mixture was diluted with dichloromethane, and the organic layer was then sequentially washed with water and saturated brine and dried over Na2SO4. The organic layer was concentrated under reduced pressure, and the resulting residue was then purified by P-TLC to give N-{4-[2-(2-cyclohexyl-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl)-ethyl]-phenyl}-acetamide (55 mg, 54.3%).

Workup

  1. washthe organic layer was then sequentially washed with water and saturated brine
  2. dry with materialdried over Na2SO4
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe resulting residue was then purified by P-TLC

Sources & evidence

ORD record
ord-007bde78496d4c7a87cfc5e7fe378630
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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