Triethylamine → HCID 58129355, compound

HRID 1949083Notes

Reaction equation

HRID 1949083 reaction equation
C[O:2][C:3]([C:5]1([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26](Cl)(=[O:28])=[O:27].CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:15]([O:14][C:12]([NH:11][C:5]1([C:3]([OH:2])=[O:4])[CH2:10][CH2:9][N:8]([S:26]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[Cl:19])(=[O:28])=[O:27])[CH2:7][CH2:6]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 14537079Methyl 4-(((1,1-dimethylethoxy)carbonyl)amino)-4-piperidinecarboxylate

Product 1

HCID 58129355HCID 58129355, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2 g (7.8 mmol) 4-tert-Butoxycarbonylamino-piperidine-4-carboxylic acid methyl ester, 1.72 g (8.1 mmol) 2-chlorobenzenesulfonyl chloride and 2.36 g (23 mmol) NEt3 in 30 mL DCM was stirred at room temperature over night. DCM and NaHCO3 aq. was added and the organic phase was dried with MgSO4 and evaporated. The ester (MS (m/e): 433.3 [(M+H)+]) was used without further purification. 3 g of the crude product was dissolved in methanol and 2.7 mL KOH aq. (5M), 30 mL water and 10 mL THF was added and the mixture was stirred at 55° C. for 5 h. The organic solvents were removed under vacuum and acetic acid was added. The mixture was extracted with ethyl acetate and the combined organic phases were washed with water, dried with MgSO4 and evaporated to yield 2.87 g of the title compound as white foam. MS (m/e): 419.1 [(M+H)+]

Workup

  1. dry with materialthe organic phase was dried with MgSO4
  2. customevaporated
  3. customThe ester (MS (m/e): 433.3 [(M+H)+]) was used without further purification
  4. dissolution3 g of the crude product was dissolved in methanol
  5. addition2.7 mL KOH aq. (5M), 30 mL water and 10 mL THF was added
  6. stirringthe mixture was stirred at 55° C. for 5 h
  7. customThe organic solvents were removed under vacuum and acetic acid
  8. additionwas added
  9. extractionThe mixture was extracted with ethyl acetate
  10. washthe combined organic phases were washed with water
  11. dry with materialdried with MgSO4
  12. customevaporated

Sources & evidence

ORD record
ord-f569321c3f3c4989839c3f6a6d6fe687
Source dataset
uspto-grants-2013_03
Patent number
US08399676B2

Reaction notes

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